Acetic Anhydride → HCID 21914905, compound

HRID 1246536Notes

Reaction equation

HRID 1246536 reaction equation
[CH3:1][S:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:6][CH:5]=1)=O.[C:19]([O-:22])(=[O:21])[CH3:20].[Na+].C(OC(=O)C)(=O)C>CCOC(C)=O>[C:19]([O:22][CH2:1][S:2][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[C:12]([NH:15][C:16](=[O:18])[CH3:17])[S:13][CH:14]=2)=[CH:6][CH:5]=1)(=[O:21])[CH3:20]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 517045Sodium AcetateHCID 21914977HCID 21914977, compound

Product 1

HCID 21914905HCID 21914905, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

N-{4-[4-(Methylsulfinyl)phenyl]-1,3-thiazol-2-yl}acetamide (1.5 g), sodium acetate (1.54 g), and acetic anhydride (30 ml) were combined under N2 atmosphere. The reaction mixture was refluxed for 2 hours. After cooled to r.t., the mixture was diluted in AcOEt. The organic solution was washed with water and brine, dried over anhydrous MgSO4, and concentrated in vacuo. The residual solid was washed with ethyl ether/n-hexane to give ({4-[2-(acetylamino)-1,3-thiazol-4-yl]phenyl}thio)methyl acetate (811.2 mg) as an off-white solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 2 hours
  2. washThe organic solution was washed with water and brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. washThe residual solid was washed with ethyl ether/n-hexane

Sources & evidence

ORD record
ord-e567023277fd41e99b20989d492d7720
Source dataset
uspto-grants-2006_10
Patent number
US07125901B2

Reaction notes

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