Phenacyl bromide → 2-({1-[(Benzyloxy)methyl]cyclobutyl}methyl)-4-phenyl-1,3-thiazole

HRID 1180767Notes

Reaction equation

HRID 1180767 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1([CH2:14][C:15](=[S:17])[NH2:16])[CH2:13][CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:18](Br)[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O>C(#N)C>[CH2:1]([O:8][CH2:9][C:10]1([CH2:14][C:15]2[S:17][CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[N:16]=2)[CH2:13][CH2:12][CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 112651762-{1-[(Benzyloxy)methyl]cyclobutyl}ethanethioamide

Product 1

HCID 112102692-({1-[(Benzyloxy)methyl]cyclobutyl}methyl)-4-phenyl-1,3-thiazoleYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 0.5 g (2.01 mmol) of 2-{1-[(benzyloxy)methyl]cyclobutyl}ethanethioamide in 10 mL of acetonitrile was added 0.39 g (2.01 mmol) of phenacyl bromide and the contents stirred at room temperature for 3 h. The mixture was concentrated under vacuum and the residue was purified by silica gel chromatography using ethyl acetate:hexane (2:8) as the eluent to afford 0.68 g (97%) of 2-({1-[(benzyloxy)methyl]cyclobutyl}methyl)-4-phenyl-1,3-thiazole as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 8.02 (s, 1H), 7.96-7.30 (m, 5H), 4.60 (s, 2H), 3.50 (s, 2H), 3.35 (s, 2H), 2.13-1.95 (m, 6H).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-26615b66b4494db0bb9cee4162b3c57f
Source dataset
uspto-grants-2007_10
Patent number
US07282512B2

Reaction notes

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