Benzyl Chloride → N-Benzylcrotonamide

HRID 1763092Notes

Reaction equation

HRID 1763092 reaction equation
[C:1]([NH2:6])(=[O:5])/[CH:2]=[CH:3]/[CH3:4].[CH2:7](Cl)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>CN(C)C=O>[CH2:7]([NH:6][C:1](=[O:5])/[CH:2]=[CH:3]/[CH3:4])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 7503Benzyl ChlorideHCID 53544872-Butenamide

Product 1

HCID 2313079N-BenzylcrotonamideYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 200 ml of N,N-dimethylformamide, were added 17 g of crotonamide, 105 g of LEVATIT MP-500, which was also used in Example 68, and 32 g of benzylchloride. They were reacted at 50° C. for 4 hours with stirring. After the reaction, the reaction solution was treated in the same manner as in Example 69, the resulting distillation residue was recrystallized from benzine, and 25 of N-benzylcrotonamide having a melting point of 112.5°-113.6° C. was obtained (yield: 71%).

Workup

  1. customThey were reacted at 50° C. for 4 hours
  2. customAfter the reaction
  3. additionthe reaction solution was treated in the same manner as in Example 69
  4. distillationthe resulting distillation residue
  5. customwas recrystallized from benzine, and 25 of N-benzylcrotonamide having a melting point of 112.5°-113.6° C.
  6. customwas obtained (yield: 71%)

Sources & evidence

ORD record
ord-0d5f89ffa64b4db3a7c5df88b628343f
Source dataset
uspto-grants-1989_05
Patent number
US04835312

Reaction notes

Loading…