Phenacyl bromide → HCID 22220823, compound

HRID 1836739Notes

Reaction equation

HRID 1836739 reaction equation
[C:1]([O:4][CH:5]([C:7]1[S:8][C:9]([CH3:13])=[C:10]([CH3:12])[N:11]=1)[CH3:6])(=O)[CH3:2].[Br:14]CC([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O>O.C(#N)C.CCOCC>[Br-:14].[CH3:13][C:9]1[S:8][C:7]2[CH:5]([CH3:6])[O:4][C:1]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:2][N+:11]=2[C:10]=1[CH3:12]

Participants

6

Reactant 2

HCID 6259Phenacyl bromideHCID 22220844HCID 22220844, compound

Product 1

HCID 22220823HCID 22220823, compoundYield 26.3%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent2×

Procedure

1-(4,5-Dimethyl-2-thiazolyl)ethyl acetate (1.28 g, 6.4 mmole), 2-bromo-1-phenyl-1-ethanone (1.28 g, 6.4 mmole), and acetonitrile (0.5 mL) were heated at 105 C. with stirring for 3.5 hr. The mixture was diluted with water (60 mL), filtered with water washes (20 mL), and the filtrate was extracted with ether (30 mL). The aqueous phase was evaporated to dryness in vacuo yielding 1.8 g crude product, which was dissolved in acetonitrile, diluted with ether, and stored at room temp. for several days to produce needle-like crystals which were recrystallized from methanol/acetonitrile/ether to give 0.57 g of the title compound, mp 236 C. (dec.).

Workup

  1. filtrationfiltered with water
  2. extraction(20 mL), and the filtrate was extracted with ether (30 mL)
  3. customThe aqueous phase was evaporated to dryness in vacuo
  4. customyielding 1.8 g crude product, which
  5. waitstored at room temp. for several days
  6. customto produce needle-like crystals which
  7. customwere recrystallized from methanol/acetonitrile/ether

Sources & evidence

ORD record
ord-b82e9ba8e1f1448981fde0850e9e6c66
Source dataset
uspto-grants-2004_08
Patent number
US06777557B2

Reaction notes

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