Chloroacetyl chloride → HCID 19913606, compound

HRID 1090617Notes

Reaction equation

HRID 1090617 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[Cl:6][C:7]1[CH:8]=[C:9]([CH:13]([CH2:15][NH:16][C:17]([CH3:20])([CH3:19])[CH3:18])[OH:14])[CH:10]=[CH:11][CH:12]=1.C(N(CC)CC)C>ClCCl>[Cl:1][CH2:2][C:3]([N:16]([CH2:15][CH:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([Cl:6])[CH:8]=1)[OH:14])[C:17]([CH3:20])([CH3:18])[CH3:19])=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 12463907HCID 12463907, compound

Product 1

HCID 19913606HCID 19913606, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chloroacetyl chloride (0.21g, 0.15ml) in dichloromethane (5ml) was added dropwise, under nitrogen to a stirred, ice-cooled solution of 3-chloro-α-[[[1,1-dimethylethyl]amino]methyl]benzenemethanol (0.5g) and triethylamine(0.38g, 0.53ml) in dichloromethane (40ml). The reaction mixture was stirred at ambient temperature for 2h., washed with hydrochloric acid (2N), brine, dried (MgSO4), evaporated and chromatographed on silica. Elution with chloroform gave α-chloro-N-[2-(3-chlorophenyl)-2-hydroxyethyl]-N-[1,1- dimethylethyl]acetamide as a colourless oil.

Workup

  1. washwashed with hydrochloric acid (2N), brine
  2. dry with materialdried (MgSO4)
  3. customevaporated
  4. customchromatographed on silica
  5. washElution with chloroform

Sources & evidence

ORD record
ord-e49128e550dc4a78bea57cf65015fc4c
Source dataset
uspto-grants-1992_01
Patent number
US05082840

Reaction notes

Loading…