Dimethylformamide → HCID 86642822, compound

HRID 1667713Notes

Reaction equation

HRID 1667713 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][C:10]([Cl:13])=[CH:9][CH:8]=2)[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:10]1[CH:9]=[CH:8][C:7]([C:5]2[N:6]=[C:2]([NH:1][C:22]3[CH:21]=[C:20]([CH:19]([O:30][CH3:31])[O:18][CH3:17])[CH:25]=[CH:24][C:23]=3[N+:26]([O-:28])=[O:27])[S:3][C:4]=2[C:14]([NH2:16])=[O:15])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 540322924-Dimethoxymethyl-2-fluoro-1-nitrobenzeneHCID 59375349HCID 59375349, compound

Product 1

HCID 86642822HCID 86642822, compoundYield 34.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.89 g (3.51 mmole) of 2-amino-4-(4-chloro-phenyl)-thiazole-5-carboxylic acid amide (V.18), 0.91 g (4.21 mmole) of 4-dimethoxymethyl-2-fluoro-1-nitrobenzene, 5.70 g (17.55 mmole) of cesium carbonate (5.70 g, 17.55 mmole) and 10 mL of dimethylformamide was heated at 70 degrees for 2 days. 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 0.55 g of 4-(4-chloro-phenyl)-2-(5-dimethoxymethyl-2-nitro-phenylamino)-thiazole-5-carboxylic acid amide (VI.19a).

Workup

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

Sources & evidence

ORD record
ord-6e04eb2a3c454cd38ff1c66d0594c925
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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