Water → N-(5-bromo-4-methyl-1,3-thiazol-2-yl)acetamide

HRID 2386174Notes

Reaction equation

HRID 2386174 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH:7][C:8](=[O:10])[CH3:9])[S:5][CH:6]=1.[Br:11]Br.O>C(O)(=O)C>[Br:11][C:6]1[S:5][C:4]([NH:7][C:8](=[O:10])[CH3:9])=[N:3][C:2]=1[CH3:1]

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 280907N-(4-Methylthiazol-2-yl)acetamide

Product 1

HCID 822437N-(5-bromo-4-methyl-1,3-thiazol-2-yl)acetamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To N-(4-methylthiazol-2-yl)acetamide (39.48 g) in acetic acid (200 ml) under a water-ice bath was added dropwise bromine (16 ml). After 2 h, water (500 ml) was added. Filtration, washing with water (3×) and drying gave N-(5-bromo-4-methylthiazol-2-yl) acetamide as off-white solid (52.13 g). H1-NMR (300 MHz, d6-DMSO) 12.27 (s, 1 H), 2.22 (s, 3 H), 2.13 (s, 3 H) ppm.

Workup

  1. filtrationFiltration
  2. washwashing with water (3×)
  3. customdrying

Sources & evidence

ORD record
ord-0d0e5602462f4e4ca9815af450f3ed94
Source dataset
uspto-grants-2012_09
Patent number
US08268818B2

Reaction notes

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