Water → HCID 178433534, compound

HRID 1905993Notes

Reaction equation

HRID 1905993 reaction equation
[Br:1]Br.[C:3]([C:6]1[S:10][C:9]([OH:11])=[N:8][C:7]=1[CH3:12])(=[O:5])[CH3:4].O>C(Cl)Cl.C(O)(=O)C>[Br:1][CH2:4][C:3]([C:6]1[S:10][C:9]([OH:11])=[N:8][C:7]=1[CH3:12])=[O:5]

Participants

6

Reactant 3

HCID 962WaterHCID 24408BromineHCID 178467558HCID 178467558, compound

Product 1

HCID 178433534HCID 178433534, compoundYield 49.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent2×

Procedure

A solution of bromine (19.2 g) in methylene chloride (10 ml) was dropwise added to a solution of 5-acetyl-2-hydroxyl-4-methylthiazol (15.7 g) in a mixture of methylene chloride (300 ml) and acetic acid (50 ml) at 40° C. to 44° C. with stirring. After being stirred at the same temperature for 30 minutes, the reaction mixture was poured into water (300 ml). The separated organic layer was washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was triturated with diisopropyl ether to give 5-(2-bromoacetyl)-2-hydroxy-4-methylthiazole (11.75 g). mp 162° C.

Workup

  1. stirringAfter being stirred at the same temperature for 30 minutes
  2. washThe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-499dceba70a24f48b00b3ca9eafd598e
Source dataset
uspto-grants-1987_03
Patent number
US04649146

Reaction notes

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