Dimethylformamide → 2-(5-Benzyloxy-2-nitro-phenylamino)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester

HRID 1667728Notes

Reaction equation

HRID 1667728 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[C:11](F)[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([O:21][C:22]([C:24]1[S:28][C:27]([NH2:29])=[N:26][C:25]=1[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=1)=[O:23])[CH3:20].CN(C)C=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O>[CH2:19]([O:21][C:22]([C:24]1[S:28][C:27]([NH:29][C:11]2[CH:10]=[C:9]([O:8][CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:14]=[CH:13][C:12]=2[N+:15]([O-:17])=[O:16])=[N:26][C:25]=1[C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=1)=[O:23])[CH3:20]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 221807044-Benzyloxy-2-fluoro-1-nitrobenzeneHCID 299233212-Amino-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester

Product 1

HCID 866428302-(5-Benzyloxy-2-nitro-phenylamino)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl esterYield 99.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2.57 g (10 mmole) of 4-benzyloxy-2-fluoro-1-nitro-benzene, 2.83 g (10 mmole) of 2-amino-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester and 20 mL of dimethylformamide was added 16.25 g (50 mmole) of cesium carbonate. The mixture was heated at 100 degrees for 1 hour. The reaction was allowed to cool to room temperature and then 500 mL of water was added. The mixture was stirred for 15 minutes and the resulting yellow solid collected by filtration to give 5.09 g of 2-(5-benzyloxy-2-nitro-phenylamino)-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid ethyl ester (VI.25).

Workup

  1. temperatureThe mixture was heated at 100 degrees for 1 hour
  2. filtrationthe resulting yellow solid collected by filtration

Sources & evidence

ORD record
ord-22ec7eab944f442897b7628fdb7b974c
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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