The present invention relates to the synthesis of N-trifluoromethylcarbonyl compounds starting from isothiocyanates, which can be converted into N-trifluoromethylcarbamoyl fluorides or similar compounds, which later on can be derivatized further to amides, ureas, carbamates, thiocarbamates and selenocarbamates.

The present invention relates to the synthesis of N-trifluoromethylcarbonyl compounds starting from isothiocyanates, which can be converted into N-trifluoromethylcarbamoyl fluorides or similar compounds, which later on can be derivatized further to amides, ureas, carbamates, thiocarbamates and selenocarbamates.

The objective of the present invention is to provide a method for producing an isocyanate compound safely and efficiently. The method for producing an isocyanate compound according to the present invention is characterized in comprising the steps of irradiating a high energy light to a halogenated methane at a temperature of 15° C. or lower in the presence of oxygen, and further adding a primary amine compound to be reacted without irradiating a high energy light.

The objective of the present invention is to provide a method for producing an isocyanate compound safely and efficiently. The method for producing an isocyanate compound according to the present invention is characterized in comprising the steps of irradiating a high energy light to a halogenated methane at a temperature of 15° C. or lower in the presence of oxygen, and further adding a primary amine compound to be reacted without irradiating a high energy light.

The present invention is directed to methods for the asymmetric synthesis of esketamine. The present invention is further directed to key intermediates in the asymmetric esketamine synthesis. In one embodiment, the invention is an asymmetric synthesis of esketamine comprising the conversion of (S)-2′-chloro-2-methoxy-3,4,5,6-5 tetrahydro-[1,1′-biphenyl]-3-yl carbamate to (S)-2′-chloro-1-isocyanato-6-methoxy-1,2,3,4-tetrahydro-1,1′-biphenyl.

##STR00001##

The present invention is directed to methods for the asymmetric synthesis of esketamine. The present invention is further directed to key intermediates in the asymmetric esketamine synthesis. In one embodiment, the invention is an asymmetric synthesis of esketamine comprising the conversion of (S)-2′-chloro-2-methoxy-3,4,5,6-5 tetrahydro-[1,1′-biphenyl]-3-yl carbamate to (S)-2′-chloro-1-isocyanato-6-methoxy-1,2,3,4-tetrahydro-1,1′-biphenyl.

##STR00001##

The invention relates to a composition excellent in stability during storage and stability during utilization, and relates to a method of producing the composition. The composition includes a compound (A) represented by general formula (1) and a compound (B) represented by general formula (2), and includes 0.00002 to 0.2 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A),
(R.sub.1—COO).sub.n—R.sub.2—(NCO).sub.m  (1)
(R.sub.1—COO).sub.n—R.sub.2—(R.sub.3—R.sub.1).sub.m  (2)
wherein in general formulae (1) and (2), R.sub.1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R.sub.2 is a (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms and optionally contains an ether group; R.sub.1 and R.sub.2 in the general formula (1) are the same as R.sub.1 and R.sub.2 in the general formula (2); in general formula (2), R.sub.3 is —NHC(═O)—; and n and m each represent an integer of one or two.

The invention relates to a composition excellent in stability during storage and stability during utilization, and relates to a method of producing the composition. The composition includes a compound (A) represented by general formula (1) and a compound (B) represented by general formula (2), and includes 0.00002 to 0.2 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A),
(R.sub.1—COO).sub.n—R.sub.2—(NCO).sub.m  (1)
(R.sub.1—COO).sub.n—R.sub.2—(R.sub.3—R.sub.1).sub.m  (2)
wherein in general formulae (1) and (2), R.sub.1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R.sub.2 is a (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms and optionally contains an ether group; R.sub.1 and R.sub.2 in the general formula (1) are the same as R.sub.1 and R.sub.2 in the general formula (2); in general formula (2), R.sub.3 is —NHC(═O)—; and n and m each represent an integer of one or two.

The invention relates to a composition excellent in stability during storage and stability during utilization, and relates to a method of producing the composition. The composition includes a compound (A) represented by general formula (1) and a compound (B) represented by general formula (2), and includes 0.00002 to 0.2 parts by mass of the compound (B) with respect to 100 parts by mass of the compound (A),
(R.sub.1—COO).sub.n—R.sub.2—(NCO).sub.m  (1)
(R.sub.1—COO).sub.n—R.sub.2—(R.sub.3—R.sub.1).sub.m  (2)
wherein in general formulae (1) and (2), R.sub.1 is an ethylenically unsaturated group having 2 to 7 carbon atoms; R.sub.2 is a (m+n)-valent hydrocarbon group having 1 to 7 carbon atoms and optionally contains an ether group; R.sub.1 and R.sub.2 in the general formula (1) are the same as R.sub.1 and R.sub.2 in the general formula (2); in general formula (2), R.sub.3 is —NHC(═O)—; and n and m each represent an integer of one or two.

The present invention relates to a process for preparing at least one ethylenically unsaturated, urethane group-containing compound from i) diisocyanate, ii) at least one compound having at least one hydroxyl group and at least one ethylenically unsaturated, polymerizable group, iii) and optionally at least one hydroxyl group-containing compound, in which 1 diisocyanate is subjected to a determination of the peroxide content immediately prior to the reaction, 2 a) if the determined peroxide content is greater than or equal to 20 mmol/kg, the diisocyanate is subjected to distillative purification until the determined peroxide content is less than 20 mmol/kg, or or b) if the determined peroxide content is less than 20 mmol/kg, no distillative purification is performed, and 3. then i) distilled diisocyanate of a) and/or untreated diisocyanate of b) is reacted with ii) at least one compound having at least one hydroxyl group and at least one ethylenically unsaturated, polymerizable group and optionally iii) with at least one hydroxyl group-containing compound to give an ethylenically unsaturated, urethane group-containing compound.