Pyridine → alpha-Bromoacetyl-beta-diethylaminostyrene

HRID 1704635Notes

Reaction equation

HRID 1704635 reaction equation
[CH2:1]([N:3]([CH2:12][CH3:13])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH3:2].N1C=CC=CC=1.[Br:20][CH2:21][C:22](Br)=[O:23]>CCOCC>[Br:20][CH2:21][C:22]([C:4]([N:3]([CH2:1][CH3:2])[CH2:12][CH3:13])=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:23]

Participants

5

Reactant 3

HCID 1049PyridineHCID 61147Bromoacetyl bromideHCID 12773281Diethylstyrylamine

Product 1

HCID 86736175alpha-Bromoacetyl-beta-diethylaminostyrene

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
5 °C

Procedure

To a solution of 17.5 g. of diethylstyrylamine in 200 ml. of ether was added 8.5 g. of pyridine. The mixture was cooled to 5° C. and a solution of 20.1 g. of bromoacetyl bromide in 200 ml. of ether was added over a period of about 4 hours. The mixture was filtered and the residue on the filter was washed with 300 ml. of ether. The combined ether filtrate and washings was washed with 1 N hydrochloric acid, 0.1 N sodium hydroxide, saturated aqueous sodium chloride, and dried over magnesium sulfate and activated carbon. The mixture was filtered and the ether was evaporated to give a quantitative yield of α-bromoacetyl-β-diethylaminostyrene. The product was shown by NMR spectrum to be a mixture of the cis and trans isomers.

Workup

  1. filtrationThe mixture was filtered
  2. washthe residue on the filter was washed with 300 ml
  3. washThe combined ether filtrate and washings was washed with 1 N hydrochloric acid, 0.1 N sodium hydroxide, saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate and activated carbon
  5. filtrationThe mixture was filtered
  6. customthe ether was evaporated

Sources & evidence

ORD record
ord-252d87e4efb34264971ba7c74e225d0d
Source dataset
uspto-grants-1978_11
Patent number
US04127581

Reaction notes

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