Chloroform → HCID 86595606, compound

HRID 2117930Notes

Reaction equation

HRID 2117930 reaction equation
C([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([NH:24][C:25](=[O:27])[CH3:26])[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1)=O.[C:28]([CH:33]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:30][CH2:31][CH3:32])=[O:29].[CH:53](Cl)(Cl)Cl>>[C:25]([NH:24][C:11]1[S:12][C:13]([C:14]2[CH:15]=[CH:16][C:17]([S:20]([CH3:23])(=[O:21])=[O:22])=[CH:18][CH:19]=2)=[C:9]([C:6]2[CH:5]=[CH:4][C:3](/[CH:53]=[CH:33]/[C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:8][CH:7]=2)[N:10]=1)(=[O:27])[CH3:26]

Participants

4

Reactant 3

HCID 6212ChloroformHCID 70670Acetic acid, 2-(triphenylphosphoranylidene)-, ethyl esterHCID 21915189HCID 21915189, compound

Product 1

HCID 86595606HCID 86595606, compound

Procedure

To a suspension of N-{4-(4-formylphenyl)-5-[4-(methylsulfonyl)phenyl]-1,3-thiazol-2-yl}acetamide (360 mg) in chloroform (7 ml) was added (carbethoxymethylene)triphenylphosphorane (626 mg) at 20° C., and the mixture was stirred for 1 h. The reaction mixture was evaporated. The residue was purified by column chromatography over silica gel (150 ml) with hexane/ethyl acetate (1:1-1:2) as an eluent to give ethyl(2E)-3-(4-{2-(acetylamino)-5-[4-(methylsulfonyl)phenyl]-1,3-thiazol-4-yl}phenyl)acrylate as a pale yellow solid.

Workup

  1. customThe reaction mixture was evaporated
  2. customThe residue was purified by column chromatography over silica gel (150 ml) with hexane/ethyl acetate (1:1-1:2) as an eluent

Sources & evidence

ORD record
ord-e0d7ab9a188a4d3fa2b1d2e5ba4c3e15
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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