Hydrochloric Acid → 3-[5-Carbamoyl-4-(3-chloro-phenyl)-thiazol-2-ylamino]-4-nitro-benzoic acid

HRID 1667697Notes

Reaction equation

HRID 1667697 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6].[NH2:14][C:15]1[S:16][C:17]([C:27]([NH2:29])=[O:28])=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[N:19]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Cl>O.CN(C)C=O>[C:27]([C:17]1[S:16][C:15]([NH:14][C:2]2[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=2[N+:11]([O-:13])=[O:12])[C:5]([OH:7])=[O:6])=[N:19][C:18]=1[C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=1)(=[O:28])[NH2:29]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 2306533-Fluoro-4-nitrobenzoic acidHCID 166588232-Amino-4-(3-chlorophenyl)thiazole-5-carboxamide

Product 1

HCID 866428143-[5-Carbamoyl-4-(3-chloro-phenyl)-thiazol-2-ylamino]-4-nitro-benzoic acidYield 55.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.222 g (1.2 mmole) of 3-fluoro-4-nitrobenzoic acid, 0.30 g (1.2 mmole) of 2-amino-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide (V.2), 1.5 g (4.6 mmole) of cesium carbonate and 40 mL of dimethylformamide was stirred at 60 degrees for 16 hours. The mixture was cooled and poured into water. The dark mixture was made acidic by addition of hydrochloric acid, and the resulting orange precipitate was collected by filtration, washing, water to give 0.281 g of 3-[5-carbamoyl-4-(3-chloro-phenyl)-thiazol-2-ylamino]-4-nitro-benzoic acid (VI.10).

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe resulting orange precipitate was collected by filtration
  3. washwashing

Sources & evidence

ORD record
ord-e666176084e943bf8b752b8c8327d63d
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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