Phenacyl bromide → HCID 1139504, compound

HRID 2422250Notes

Reaction equation

HRID 2422250 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.[CH2:11]([NH:15][C:16]([NH2:18])=[S:17])[CH:12]([CH3:14])[CH3:13].C(=O)([O-])O.[Na+]>CN(C)C=O>[CH2:11]([NH:15][C:16]1[S:17][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[N:18]=1)[CH:12]([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 516892Sodium BicarbonateHCID 853362Isobutylthiourea

Product 1

HCID 1139504HCID 1139504, compoundYield 72.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-bromo-1-phenylethanone (4.0 g), N-isobutylthiourea (2.60 g) and N,N-dimethylformamide (15 mL) was stirred at room temperature for 1 hr. The reaction mixture was poured into saturated aqueous sodium hydrogencarbonate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was concentrated, and the residue was purified by silica gel column chromatography with ethyl acetate-hexane (gradient of 1:9 to 2:1 by volume ratio) to give the title compound (3.30 g, 71%) as a yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. concentrationThe ethyl acetate layer was concentrated
  3. customthe residue was purified by silica gel column chromatography with ethyl acetate-hexane (gradient of 1:9 to 2:1 by volume ratio)

Sources & evidence

ORD record
ord-dcfb5901732b48a489256ac110298e62
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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