Phosgene → HCID 11964606, compound

HRID 2069267Notes

Reaction equation

HRID 2069267 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 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).

Workup

  1. additionare added at −15° C
  2. temperaturesimultaneously heating
  3. temperatureAt reflux
  4. waitreplaced by a stream of argon for an additional hour
  5. distillationThe toluene is distilled off

Sources & evidence

ORD record
ord-7c8f79de68184ad6bbcdbbe9d4f045df
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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