Phenacyl bromide → HCID 22220747, compound

HRID 1836726Notes

Reaction equation

HRID 1836726 reaction equation
[C:1]([O:9][CH:10]([C:12]1[S:13][CH:14]=[CH:15][N:16]=1)[CH3:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17][CH2:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:20].C(#N)C>ClCCl>[Br-:17].[O:20]=[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:18][N+:16]1[CH:15]=[CH:14][S:13][C:12]=1[CH:10]([O:9][C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH3:11]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 6342AcetonitrileHCID 22220778HCID 22220778, compound

Product 1

HCID 22220747HCID 22220747, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-Thiazolyl)ethyl benzoate (2.0 g, 8.5 mmole), 2-bromo-1-phenyl-1-ethanone (1.7 g, 8.5 mmole), and acetonitrile (0.4 mL) were combined and heated at 115 C. with stirring for 3 hr. After cooling, the reaction was diluted with 50 mL dichloromethane and extracted with 5×30 mL water. The combined, filtered water layers were evaporated to yield 2.2 g crude product, which crystallized from acetonitrile/ether after several days to afford 1.22 g of the title compound, mp 130-131.5 C.

Workup

  1. temperatureheated at 115 C
  2. temperatureAfter cooling
  3. extractionextracted with 5×30 mL water
  4. filtrationfiltered water layers
  5. customwere evaporated
  6. customto yield 2.2 g crude product, which
  7. customcrystallized from acetonitrile/ether after several days

Sources & evidence

ORD record
ord-e51b79ef31e44f2690c7e57487fc7196
Source dataset
uspto-grants-2004_08
Patent number
US06777557B2

Reaction notes

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