Dimethylformamide → 4-(2-Chloro-phenyl)-2-(5-dimethoxymethyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid amide

HRID 1667715Notes

Reaction equation

HRID 1667715 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:14]([NH2:16])=[O:15])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[Cl:13])[N:6]=1.[CH3:17][O:18][CH:19]([O:30][CH3:31])[C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[C:22](F)[CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>C(OCC)(=O)C.O>[Cl:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[C:5]1[N:6]=[C:2]([NH:1][C:22]2[CH:21]=[C:20]([CH:19]([O:30][CH3:31])[O:18][CH3:17])[CH:25]=[CH:24][C:23]=2[N+:26]([O-:28])=[O:27])[S:3][C:4]=1[C:14]([NH2:16])=[O:15]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 540322924-Dimethoxymethyl-2-fluoro-1-nitrobenzeneHCID 59375354HCID 59375354, compound

Product 1

HCID 866428254-(2-Chloro-phenyl)-2-(5-dimethoxymethyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid amideYield 89.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.15 g (0.60 mmole) of 2-amino-4-(2-chloro-phenyl)-thiazole-5-carboxylic acid amide (V.20), 0.15 g (0.72 mmole) of 4-dimethoxymethyl-2-fluoro-1-nitrobenzene, 0.99 g (3.0 mmole) of cesium carbonate and 10 mL of dimethylformamide was heated at 70 degrees for one day. The reaction mixture was diluted with ethyl acetate and water. The precipitate was collected by filtration, washed with water and dried under vacuum to give 0.24 g of 4-(2-chloro-phenyl)-2-(5-dimethoxymethyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid amide (VI.20a).

Workup

  1. temperaturewas heated at 70 degrees for one day
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with water
  4. customdried under vacuum

Sources & evidence

ORD record
ord-0dee18c69e11413e9e0b6455246a4ed1
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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