Phenacyl bromide → HCID 22220812, compound

HRID 1836725Notes

Reaction equation

HRID 1836725 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]([OH:8])[CH3:7].[Br:9][CH2:10][C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:12].C(#N)C>O>[Br-:9].[O:12]=[C:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][N+:3]1[CH:4]=[CH:5][S:1][C:2]=1[CH:6]([OH:8])[CH3:7]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 6342AcetonitrileHCID 99892952-Thiazolemethanol, alpha-methyl- (7CI,9CI)

Product 1

HCID 22220812HCID 22220812, compoundYield 42.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-(2-Thiazolyl)ethanol (0.71 g, 5.49 mmole), 2-bromo-1-phenyl-1-ethanone (1.09 g, 5.47 mmole), and acetonitrile (0.6 mL) were combined and heated with stirring at 130 C. for 4 hr. After cooling, water (20 mL) was added and the mixture was filtered and extracted twice with ether. The aqueous layer was treated with active carbon and filtered to give a clear solution which was concentrated in vacuo to 1.52 g of residue, which was crystallized from acetonitrile/ether and recrystallized twice from methanol/acetonitrile/ether to give 0.77 g of the title compound as prisms, mp 157-158 C; calc'd for C13H14NO2SBr: C 47.55, H 4.33, N 4.26; found: C 47.52, H 4.32, N 4.14.

Workup

  1. temperatureheated
  2. temperatureAfter cooling
  3. filtrationthe mixture was filtered
  4. extractionextracted twice with ether
  5. additionThe aqueous layer was treated with active carbon
  6. filtrationfiltered
  7. customto give a clear solution which
  8. concentrationwas concentrated in vacuo to 1.52 g of residue, which
  9. customwas crystallized from acetonitrile/ether
  10. customrecrystallized twice from methanol/acetonitrile/ether

Sources & evidence

ORD record
ord-14e9245a634e4a2c95a2f02b7aecd3ea
Source dataset
uspto-grants-2004_08
Patent number
US06777557B2

Reaction notes

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