Acetic Anhydride → HCID 21914905, compound

HRID 2117947Notes

Reaction equation

HRID 2117947 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-200449dd3c964ba3850dd22a95e4d8d7
Source dataset
uspto-grants-2008_10
Patent number
US07442715B2

Reaction notes

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