Acetic Anhydride → N-(4-Methylthiazol-2-yl)acetamide

HRID 1715182Notes

Reaction equation

HRID 1715182 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([CH3:14])[N:13]=1>>[CH3:14][C:12]1[N:13]=[C:9]([NH:8][C:5](=[O:7])[CH3:6])[S:10][CH:11]=1

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 741432-Amino-4-methylthiazole2×

Product 1

HCID 280907N-(4-Methylthiazol-2-yl)acetamide

Conditions

Temperature
5 °C

Procedure

To a stirred, cooled (5° C.) solution of acetic anhydride (237 ml, 2.51 mol) is added portionwise 2-amino-4-methyl thiazole (80 g, 0.697 mol). To allow dissolution of the 2-amino-4-methyl thiazole, the reaction mixture is allowed to warm but kept below 35° C. Once a solution forms, the reaction mixture is cooled to 5° C. and stirred overnight. The solvent is removed in vacuo and the solid is dried in a vacuum oven overnight. The resulting solid is triturated with iso-hexane (100 ml) and dried again. Recrystallisation from EtOAc/iso-hexane affords the title product as a pale yellow solid.

Workup

  1. temperatureto warm
  2. customkept below 35° C
  3. customThe solvent is removed in vacuo
  4. customthe solid is dried in a vacuum oven overnight
  5. customThe resulting solid is triturated with iso-hexane (100 ml)
  6. customdried again
  7. customRecrystallisation from EtOAc/iso-hexane

Sources & evidence

ORD record
ord-aa5a3ec38b07494c9f7a26173d45aa47
Source dataset
uspto-grants-2010_09
Patent number
US07799810B2

Reaction notes

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