Phosgene → HCID 11964606, compound
Reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[NH2:17].[C:19](Cl)(Cl)=[O:20]>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[C:7]([C:13]([F:16])([F:15])[F:14])=[CH:6][C:5]=1[N:17]=[C:19]=[O:20]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a suspension of 100 mg (0.379 mmol) of 2-amino-5-nitro-4-trifluoromethyl-benzoic acid methyl ester in 1.5 ml of dry toluene 1.5 ml of a 20% solution of phosgene in toluene are added at −15° C. After warming to room temperature, a stream of phosgene is introduced into the suspension and simultaneously heating is started. At reflux, the stream of phosgene is maintained for one hour, then replaced by a stream of argon for an additional hour. The toluene is distilled off leaving 110 mg (100%) of 2-isocyanato-5-nitro-4-trifluoromethyl-benzoic acid methyl ester as a beige solid. IR (CHCl3): 2260 cm−1 (s). 1H-NMR (CDCl3, 360 MHz): 4.05 (s, 3H); 7.55 (s, 1H); 8.65 (s, 1H).