Phosgene → HCID 11964606, compound

HRID 906563Notes

Reaction equation

HRID 906563 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

HCID 6371Phosgene3×HCID 11965778Methyl 2-amino-5-nitro-4-(trifluoromethyl)benzoate

Product 1

HCID 11964606HCID 11964606, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a suspension of 2-amino-5-nitro-4-trifluoromethyl-benzoic acid methyl ester (100 mg, 0.379 mmol) in dry toluene (1.5 mL) was added a solution of phosgene in toluene (20%, 1.5 mL) at −15° C. After warming to r.t., a stream of phosgene was introduced into the suspension and simultaneously heating was started. At reflux, the stream of phosgene was maintained for one hour, then replaced by a stream of argon for an additional hour. The toluene was distilled off leaving 2-isocyanato-5-nitro-4-trifluoromethyl-benzoic acid methyl ester (110 mg, 100%) 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).

Workup

  1. temperaturesimultaneously heating
  2. temperatureAt reflux
  3. waitreplaced by a stream of argon for an additional hour
  4. distillationThe toluene was distilled off

Sources & evidence

ORD record
ord-37a1b596bf4b4ab5a9db261692af2016
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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