Phenacyl bromide → HCID 22220752, compound

HRID 1836736Notes

Reaction equation

HRID 1836736 reaction equation
[C:1]([O:4][CH:5]([C:7]1[S:8][CH:9]=[CH:10][N:11]=1)[CH3:6])(=[O:3])[CH3:2].[Br:12][CH2:13][C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15]>C(#N)C.CCOCC>[Br-:12].[O:15]=[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH2:13][N+:11]1[CH:10]=[CH:9][S:8][C:7]=1[CH:5]([O:4][C:1](=[O:3])[CH3:2])[CH3:6]

Participants

5

Reactant 2

HCID 6259Phenacyl bromideHCID 13678542HCID 13678542, compound

Product 1

HCID 22220752HCID 22220752, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

1-(2-Thiazolyl)ethyl acetate (0.8 g, 4.67 mmole) and 2-bromo-1-phenyl-1-ethanone (0.93 g, 4.67 mmole) were combined and stirred at room temp. for 5 days. The viscous mixture was dissolved in acetonitrile (5 mL), diluted with ether (3 mL), and stored overnight at 4 C. The resulting crystals (1.5 g) were recrystallized from acetonitrile/ether to afford 0.97 g of the title compound, mp 155-156 C.

Workup

  1. waitstored overnight at 4 C
  2. customThe resulting crystals (1.5 g) were recrystallized from acetonitrile/ether

Sources & evidence

ORD record
ord-175ec0896a7d4513adcce86bf82b436a
Source dataset
uspto-grants-2004_08
Patent number
US06777557B2

Reaction notes

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