Diisopropyl Ether → 2-Amino-5-bromo-4-methyl-1,3-thiazole hydrochloride

HRID 1656934Notes

Reaction equation

HRID 1656934 reaction equation
[ClH:1].[NH2:2][C:3]1[S:4][CH:5]=[C:6]([CH3:8])[N:7]=1.[Br:9]N1C(=O)CCC1=O.C(OC(C)C)(C)C>C(O)(=O)C>[ClH:1].[NH2:2][C:3]1[S:4][C:5]([Br:9])=[C:6]([CH3:8])[N:7]=1

Participants

5

Reactant 3

HCID 7914Diisopropyl EtherHCID 67184N-bromobutanimideHCID 802402-Thiazolamine, 4-methyl-, hydrochloride (1:1)

Product 1

HCID 189547282-Amino-5-bromo-4-methyl-1,3-thiazole hydrochlorideYield 89.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-amino-4-methylthiazole hydrochloride (3.0 g) in acetic acid (20 ml) was added once N-bromosuccinimide (4.0 g) at room temperature with stirring. The mixture was stirred at room temperature for 1.5 hours and the reaction mixture was poured into isopropyl ether under ice cooling. The precipitates were collected by filtration, washed with ethyl ether and dried in vacuo to give 2-amino-5-bromo-4-methylthiazole hydrochloride (4.1 g, yield: 89.1%).

Workup

  1. stirringThe mixture was stirred at room temperature for 1.5 hours
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with ethyl ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-5e4a4947972144dcb8057233d69acbbd
Source dataset
uspto-grants-1993_10
Patent number
US05256675

Reaction notes

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