Triethylamine → 2-bromopropionic acid N-cyano-N-butylamide

HRID 845695Notes

Reaction equation

HRID 845695 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](Br)=[O:4].[CH2:7]([NH:11][C:12]#[N:13])[CH2:8][CH2:9][CH3:10].C(N(CC)CC)C>CCOCC>[C:12]([N:11]([CH2:7][CH2:8][CH2:9][CH3:10])[C:3](=[O:4])[CH:2]([Br:1])[CH3:6])#[N:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 79047Propanoyl bromide, 2-bromo-HCID 12295218Butylcyanamide

Product 1

HCID 538690972-bromopropionic acid N-cyano-N-butylamideYield 70.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

29.5 g (0.137 mole) of 2-bromopropionyl bromide are added dropwise at 15° C. to 13.4 g (0.137 mole) of butyl cyanamide and 13.8 g (0.137 mole) of triethylamine in 150 ml of ether. The mixture is stirred for 3 hours at 20° to 25° C., then filtered to remove the precipitated salt. The filtrate is extracted with dilute hydrochloric acid and the extract is dried over sodium sulfate and concentrated by evaporation. The oily residue is distilled under high vacuum, affording 22.6 g (70.8% of theory) of 2-bromopropionic acid N-cyano-N-butylamide with a boiling point of 53°-54° C. at 0.0052 mbar.

Workup

  1. filtrationfiltered
  2. customto remove the precipitated salt
  3. extractionThe filtrate is extracted with dilute hydrochloric acid
  4. dry with materialthe extract is dried over sodium sulfate
  5. concentrationconcentrated by evaporation
  6. distillationThe oily residue is distilled under high vacuum

Sources & evidence

ORD record
ord-122e0641a6c54ab6b11527a005f8408d
Source dataset
uspto-grants-1988_07
Patent number
US04759796

Reaction notes

Loading…