Phosgene → 211374-80-0

HRID 1864055Notes

Reaction equation

HRID 1864055 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4](O)=[O:5].O1CCCC1.C(Cl)(Cl)=O.[OH-].[NH4+:23]>C1(C)C=CC=CC=1>[NH2:1][C:2]1[CH:10]=[C:9]([F:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4]([NH2:23])=[O:5]

Participants

6

Reactant 4

HCID 6371PhosgeneHCID 8028TetrahydrofuranHCID 14923Ammonium HydroxideHCID 7359652-Amino-4,5-difluorobenzoic acid

Product 1

HCID 16640510211374-80-0Yield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A round-bottomed flask was charged with 2-amino-4,5-difluorobenzoic acid (2 g, 11.7 mmol) and 50 mL tetrahydrofuran (THF). The flask was cooled to 0° C., whereupon a 20% solution of phosgene (6.11 mL, 11.7 mmol) in toluene was added dropwise. The reaction was stirred for 15 min at 0° C., after which a large stoichiometric excess of ammonium hydroxide was added. The reaction was then warmed to room temperature, stirred for 18 h, then washed with water, and then extracted three times with ethyl acetate. Organic layers were combined and dried over sodium sulfate, then concentrated. The product was identified as 2-amino-4,5-difluorobenzamide (1.24 g, 7.2 mmol, 62% yield). MS: M(C7H6F2N2O)=172.13, (M+H)+=173.2.

Workup

  1. additionwas added dropwise
  2. temperatureThe reaction was then warmed to room temperature
  3. stirringstirred for 18 h
  4. washwashed with water
  5. extractionextracted three times with ethyl acetate
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-7456f819015f4fe8a803d26291eba949
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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