Ammonia → N-Benzylacrylamide

HRID 1732223

Reaction equation

HRID 1732223 reaction equation
O[CH2:2][CH2:3][C:4]([NH2:6])=[O:5].[CH2:7](N)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.N>C(C1C(O)=C(C(C)(C)C)C=C(C)C=1)(C)(C)C>[CH2:7]([NH:6][C:4](=[O:5])[CH:3]=[CH2:2])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 7504BenzylamineHCID 41451403-Hydroxypropanamide

Product 1

HCID 139428N-BenzylacrylamideYield 86.2%

Reagents, catalysts & solvents 1

HCID 314042,6-Di-tert-butyl-4-methylphenolCatalyst

Procedure

59 g of β-hydroxypropionamide and 75 g of benzylamine were heated with 50 mg of 2,6-di-t-butyl-p-cresol for 7 hours in a temperature range of 120°-170° C. until the evolution of ammonia was complete. After adding 2.2 g of polyphosphoric acid distillation was carried out in an oil pump vacuum; the subsequent redistillation with the addition of 1 ml of sulphuric acid yielded 92 g of N-benzylacrylamide, Bp0.1 113° C., which crystallized in the receiver. Mp (crude product): 53° C.

Workup

  1. additionAfter adding
  2. distillation2.2 g of polyphosphoric acid distillation
  3. distillationthe subsequent redistillation
  4. additionwith the addition of 1 ml of sulphuric acid

Sources & evidence

ORD record
ord-344fc3d640a84449bbb4702a45accb0e
Source dataset
uspto-grants-1980_12
Patent number
US04237067

Linked notes

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