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

HRID 1667677Notes

Reaction equation

HRID 1667677 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH2:11])=[N:8][C:7]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5])[CH3:2].[CH3:18][O:19][CH:20]([O:31][CH3:32])[C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[C:23](F)[CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C)C=O>O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([NH:11][C:23]2[CH:22]=[C:21]([CH:20]([O:31][CH3:32])[O:19][CH3:18])[CH:26]=[CH:25][C:24]=2[N+:27]([O-:29])=[O:28])=[N:8][C:7]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 73239Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylateHCID 540322924-Dimethoxymethyl-2-fluoro-1-nitrobenzene

Product 1

HCID 866428042-(5-Dimethoxymethyl-2-nitro-phenylamino)-4-phenyl-thiazole-5-carboxylic acid ethyl esterYield 54.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 0.250 g (1 mmole) of 2-amino-4-phenyl-thiazole-5-carboxylic acid ethyl ester (V.1), 0.215 g (1 mmole) of 4-dimethoxymethyl-2-fluoro-1-nitro-benzene, 0.488 g (1.5 mmole) of cesium carbonate and 5 mL of dimethylformamide was heated at 100 degrees overnight. The cooled mixture was diluted with 30 mL of water and then extracted three times with 20 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography, eluting with ethyl acetate-hexanes (gradient 0:100-10:90) to give 0.240 g of 2-(5-dimethoxymethyl-2-nitro-phenylamino)-4-phenyl-thiazole-5-carboxylic acid ethyl ester (VIA a) as an orange solid.

Workup

  1. temperaturewas heated at 100 degrees overnight
  2. extractionextracted three times with 20 mL of ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with ethyl acetate-hexanes (gradient 0:100-10:90)

Sources & evidence

ORD record
ord-209deecfd88e4b9cae5e5829a02b08b4
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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