Cesium carbonate → 4-(3-Chloro-phenyl)-2-[5(2,2-dimethoxy-ethyl)-2-nitro-phenylamino]-thiazole-5-carboxylic acid amide

HRID 1667694Notes

Reaction equation

HRID 1667694 reaction equation
[CH3:1][O:2][CH:3]([O:15][CH3:16])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[C:7](F)[CH:6]=1.[NH2:17][C:18]1[S:19][C:20]([C:30]([NH2:32])=[O:31])=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=2)[N:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[NH4+]>CN(C)C=O>[Cl:29][C:25]1[CH:24]=[C:23]([C:21]2[N:22]=[C:18]([NH:17][C:7]3[CH:6]=[C:5]([CH2:4][CH:3]([O:15][CH3:16])[O:2][CH3:1])[CH:10]=[CH:9][C:8]=3[N+:11]([O-:13])=[O:12])[S:19][C:20]=2[C:30]([NH2:32])=[O:31])[CH:28]=[CH:27][CH:26]=1

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 166588232-Amino-4-(3-chlorophenyl)thiazole-5-carboxamideHCID 674283784-(2,2-Dimethoxy-ethyl)-2-fluoro-1-nitro-benzene

Product 1

HCID 866428114-(3-Chloro-phenyl)-2-[5(2,2-dimethoxy-ethyl)-2-nitro-phenylamino]-thiazole-5-carboxylic acid amideYield 51.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 0.625 g (2.73 mmole) of 4-(2,2-dimethoxy-ethyl)-2-fluoro-1-nitro-benzene (IV.9b), 0.630 g (2.73 mmole) of 2-amino-4-(3-chloro-phenyl)-thiazole-5-carboxylic acid amide (V.2), 2.66 g (8.2 mmole) of cesium carbonate and 10 mL of dimethylformamide was stirred at 60 degrees for 3 hours. The mixture was cooled, poured into 50 mL of dilute ammonium chloride solution. The resulting suspension was extracted three times with 20 mL of ethyl acetate. The combined organic layers were washed three times with 20 mL of water, once with 20 mL of brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was triturated with diethyl ether to give 0.650 g of 4-(3-chloro-phenyl)-2-[5(2,2-dimethoxy-ethyl)-2-nitro-phenylamino]-thiazole-5-carboxylic acid amide (VI.9a) as an orange solid.

Workup

  1. temperatureThe mixture was cooled
  2. extractionThe resulting suspension was extracted three times with 20 mL of ethyl acetate
  3. washThe combined organic layers were washed three times with 20 mL of water
  4. dry with materialonce with 20 mL of brine, dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-e2fce7b234524b068d27e202768ac30c
Source dataset
uspto-grants-2011_10
Patent number
US08044213B2

Reaction notes

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