Acetic Anhydride → N-(4-Bromo-1,3-thiazol-2-yl)acetamide

HRID 1051593Notes

Reaction equation

HRID 1051593 reaction equation
[Br:1][C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.[C:8](OC(=O)C)(=[O:10])[CH3:9]>C(O)(=O)C>[Br:1][C:2]1[N:3]=[C:4]([NH:7][C:8](=[O:10])[CH3:9])[S:5][CH:6]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 4280244-Bromo-1,3-thiazol-2-amine

Product 1

HCID 57841264N-(4-Bromo-1,3-thiazol-2-yl)acetamideYield 49%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4-bromothiazol-2-amine (0.500 g, 2.81 mmol), acetic anhydride (0.43 mL, 4.50 mmol) and acetic acid (5 mL) was refluxed for 2 h. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was purified via column chromatography on silica gel (eluting with 25% ethyl acetate-petroleum ether) to afford N-(4-bromothiazol-2-yl)acetamide (0.300 g, 49%) as a white solid. MS (ESI, pos. ion) m/z 221, 223 [M+H]+.

Workup

  1. concentrationconcentrated under vacuum
  2. customThe residue was purified via column chromatography on silica gel (eluting with 25% ethyl acetate-petroleum ether)

Sources & evidence

ORD record
ord-5bbe1778e34c4e3882b70b9e57e85e56
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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