Triethylamine → HCID 11469634, compound

HRID 1078418Notes

Reaction equation

HRID 1078418 reaction equation
[C:1](Cl)(=[O:4])[CH:2]=[CH2:3].[Cl:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][NH2:12])=[CH:9][CH:8]=1.C(N(CC)CC)C>ClCCl>[Cl:6][C:7]1[CH:14]=[CH:13][C:10]([CH2:11][NH:12][C:1](=[O:4])[CH:2]=[CH2:3])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 660364-Chlorobenzylamine

Product 1

HCID 11469634HCID 11469634, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acryloyl chloride (86.9 g) was added dropwise with stirring to a solution of 4-chlorobenzylamine (135.8 g) and triethylamine (133.5 ml) in dichloromethane (500 ml) at -15 to -20° C., under nitrogen. After the addition the mixture was stirred at ambient temperature for 2.5 hours. The mixture was washed with dilute aqueous sodium hydroxide solution and then with water. The dichloromethane solution was dried and evaporated under reduced pressure. The solid residue was recrystallised from ethyl acetate to give N-(4-chlorobenzyl)acrylamide, m.p. 103°-104° C.

Workup

  1. additionAfter the addition the mixture
  2. washThe mixture was washed with dilute aqueous sodium hydroxide solution
  3. dry with materialThe dichloromethane solution was dried
  4. customevaporated under reduced pressure
  5. customThe solid residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-04d05aaf6c6d46e5a6f6642ec889ad41
Source dataset
uspto-grants-1996_08
Patent number
US05547972

Reaction notes

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