Glycinamide → HCID 86734779, compound

HRID 2398819Notes

Reaction equation

HRID 2398819 reaction equation
[NH2:1][CH2:2][C:3]([NH2:5])=[O:4].CC[O-].[Na+].[CH2:10](Br)[CH:11]=[CH:12][CH3:13].[Br-].[Na+]>C(O)C>[CH2:10]([NH:5][C:3](=[O:4])[CH2:2][NH2:1])[CH:11]=[CH:12][CH3:13]

Participants

6

Reactant 4

HCID 69020GlycinamideHCID 1224142-Butene, 1-bromo-HCID 253881Sodium BromideHCID 2723922Sodium ethoxide

Product 1

HCID 86734779HCID 86734779, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

7.4 g of glycine amide and 6.8 g of sodium ethylate were charged into a 100 ml four-necked flask, and 30 ml of ethyl alcohol was added to the mixture. To the resulting solution was then added dropwise 13.5 g of crotyl bromide over a period of one hour at room temperature. After completion of the addition, the mixture was heated at a temperature of 50° C. for 2 hours. After completion of the reaction, sodium bromide which precipitated upon cooling the reaction mixture was removed by filtration and the solvent was removed by distillation under reduced pressure to obtain 10.3 g of the desired N-crotylglycine amide as a pale yellow oily substance having nD23.5 1.4991.

Workup

  1. additionAfter completion of the addition
  2. customprecipitated
  3. temperatureupon cooling the reaction mixture
  4. customwas removed by filtration
  5. customthe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-1c5587e8cf6f4e6fa9a62c94169ac4d4
Source dataset
uspto-grants-1977_05
Patent number
US04025651

Reaction notes

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