Water → HCID 19375937, compound

HRID 2211157Notes

Reaction equation

HRID 2211157 reaction equation
B(Br)(Br)Br.C[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]=[C:15]([C:18]([NH2:20])=[O:19])[S:16][CH:17]=2)=[CH:9][CH:8]=1.O>ClCCl>[OH:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[N:14]=[C:15]([C:18]([NH2:20])=[O:19])[S:16][CH:17]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 19375903HCID 19375903, compound

Product 1

HCID 19375937HCID 19375937, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (3.7 ml) was added dropwise under nitrogen to a suspension of 4-(4-methoxyphenyl)-thiazole-2-carboxamide (3 g) in dichloromethane (45 ml). The mixture was stirred at room temperature for 2 h, then under reflux for 2 h and then cooled, after which water (60 ml) was added cautiously. The precipitate was filtered and the collected solid was dried under vacuum at 50° C., and recrystallised from methanol to give 4-(4-hydroxyphenyl)-thiazole-2-carboxamide (2.03 g), m.p. 223°-227° C.

Workup

  1. temperatureunder reflux for 2 h
  2. temperaturecooled
  3. filtrationThe precipitate was filtered
  4. customthe collected solid was dried under vacuum at 50° C.
  5. customrecrystallised from methanol

Sources & evidence

ORD record
ord-6818e9cdd4cc48ca82a65114a33ab562
Source dataset
uspto-grants-1995_10
Patent number
US05462959

Reaction notes

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