Ammonia → 2,6-Di-tert-butyl-4-(imidazo[2,1-b][1,3]thiazol-6-yl)phenol

HRID 980351Notes

Reaction equation

HRID 980351 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[C:7]([C:11]1[CH:12]=[C:13]([CH:18]=[C:19]([C:22]([CH3:25])([CH3:24])[CH3:23])[C:20]=1[OH:21])[C:14](=O)[CH2:15]Br)([CH3:10])([CH3:9])[CH3:8].N.O>C(O)C>[C:22]([C:19]1[CH:18]=[C:13]([C:14]2[N:1]=[C:2]3[N:6]([CH:15]=2)[CH:5]=[CH:4][S:3]3)[CH:12]=[C:11]([C:7]([CH3:10])([CH3:9])[CH3:8])[C:20]=1[OH:21])([CH3:25])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 21552-AminothiazoleHCID 6161612-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-one

Product 1

HCID 131731732,6-Di-tert-butyl-4-(imidazo[2,1-b][1,3]thiazol-6-yl)phenolYield 38.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 20 ml of ethanol were dissolved 1.2 g of 2-aminothiazole and 3.9 g of 3,5-di-tert-butyl-4-hydroxyphenacyl bromide, and the solution was refluxed for 2 hours. The reaction mixture was neutralized by the addition of aqueous ammonia and added 30 ml of water. The crystals thus precipitated were recovered by filtration and recrystallized from ethanol to provide 1.5 g of 6-(3,5-di-tert-butyl-4-hydroxyphenyl)imidazo[2,1-b]thiazole.

Workup

  1. temperaturethe solution was refluxed for 2 hours
  2. customThe crystals thus precipitated
  3. filtrationwere recovered by filtration
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-a588a04e205a43e2a814ef328f5b8266
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

Loading…