Phenacyl bromide → HCID 22284323, compound

HRID 1061666Notes

Reaction equation

HRID 1061666 reaction equation
C(N(CC)CC)C.[SH:8][CH2:9][C:10]([NH2:12])=[O:11].[CH2:13](Br)[C:14]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=O>C(O)C>[C:16]1([C:14]2[NH:12][C:10](=[O:11])[CH2:9][S:8][CH:13]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 129612-Mercaptoacetamide

Product 1

HCID 22284323HCID 22284323, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Triethylamine (4.55 g) is added to a solution of 2-mercaptoacetamide (8.00 g, Reference compound No. 40-1) in ethanol (70 ml), then phenacyl bromide (17.5 g) is added to the mixture, and the whole is stirred for four hours. The reaction mixture is concentrated under reduced pressure, water and 0.1 N hydrochloric acid are added to the resulting residue, and the whole is extracted with ethyl acetate. The extract is washed with saturated brine and dried over anhydrous magnesium sulfate. The extract is concentrated under reduced pressure. The resulting residue is suspended in ethanol (200 ml), p-toluenesulfonic acid monohydrate (catalytic amount) is added to the suspension, and the mixture is refluxed for five days. The reaction mixture is cooled to room temperature to precipitate crystals. The crystals are filtered off and washed with ethanol to give the titled reference compound (11.6 g).

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure, water and 0.1 N hydrochloric acid
  2. additionare added to the resulting residue
  3. extractionthe whole is extracted with ethyl acetate
  4. washThe extract is washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe extract is concentrated under reduced pressure
  7. additionp-toluenesulfonic acid monohydrate (catalytic amount) is added to the suspension
  8. temperaturethe mixture is refluxed for five days
  9. customto precipitate crystals
  10. filtrationThe crystals are filtered off
  11. washwashed with ethanol

Sources & evidence

ORD record
ord-9b6d8e40e6d7468693c38672ecfd7465
Source dataset
uspto-grants-2005_11
Patent number
US06960575B2

Reaction notes

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