Ammonia → 4-[4-(Imidazol-1-ylmethyl)-thiazol-2-yl]-phenol

HRID 854686

Reaction equation

HRID 854686 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][CH:11]=[C:12]([CH2:14][N:15]3[CH:19]=[CH:18][N:17]=[CH:16]3)[N:13]=2)=[CH:5][CH:4]=1.N>Br>[N:15]1([CH2:14][C:12]2[N:13]=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([OH:2])=[CH:4][CH:5]=3)[S:10][CH:11]=2)[CH:19]=[CH:18][N:17]=[CH:16]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 694286851-[2-(4-Methoxy-phenyl)-thiazol-4-ylmethyl]-imidazole

Product 1

HCID 1363552334-[4-(Imidazol-1-ylmethyl)-thiazol-2-yl]-phenolYield 85.5%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 0.54 g (2.0 mmol) 1-[2-(4-methoxy-phenyl)-thiazol-4-ylmethyl]-imidazole in 15 ml 47% aqueous hydrobromic acid was stirred at 70° C. for 4 days. The reaction mixture was poured on ice, made basic with concentrated ammonia and extracted with ethyl acetate to yield 0.44 g (85%) raw 4-[4-(imidazol-1-ylmethyl)-thiazol-2-yl]-phenol as tan crystals.

Workup

  1. additionThe reaction mixture was poured on ice
  2. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-e53883339a67453d9791bc4ca221695e
Source dataset
uspto-grants-2007_08
Patent number
US07259262B2

Linked notes

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