Phenacyl bromide → HCID 22220803, compound

HRID 1836738Notes

Reaction equation

HRID 1836738 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH:8]([OH:10])[CH3:9])[S:5][C:6]=1[CH3:7].[Br:11][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14]>C(#N)C>[Br-:11].[CH3:1][C:2]1[N+:3]([CH2:12][C:13](=[O:14])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:4]([CH:8]([OH:10])[CH3:9])[S:5][C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 222208677531-72-8

Product 1

HCID 22220803HCID 22220803, compoundYield 33.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(4,5-dimethyl-2-thiazolyl)ethanol (0.24 g, 1.5 mmole), 2-bromo-1-phenyl-1-ethanone (0.3 g, 1.5 mmole) and acetonitrile (0.1 mL) were heated at 45° C. with stirring for 1 hr, then stored at 37° C. for 20 hr, and at 25° C. for 26 hr. The partially solidified mixture was washed with ether and acetonitrile-ether to give 0.25 g of crude product which was recrystalized from acetonitrile-ether to give 0.18 g of the title compound, mp 174-176° C. Calcd for C15H18NO2SBr: C 50.57; H 5.09; N 3.93. Found, C 50.37; H 5.09; N 3.88.

Workup

  1. waitstored at 37° C. for 20 hr
  2. waitat 25° C. for 26 hr
  3. washThe partially solidified mixture was washed with ether and acetonitrile-ether
  4. customto give 0.25 g of crude product which
  5. customwas recrystalized from acetonitrile-ether

Sources & evidence

ORD record
ord-014704c800af4111888e5cd75bfe3722
Source dataset
uspto-grants-2004_08
Patent number
US06777557B2

Reaction notes

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