Chloroacetyl chloride → HCID 19913606, compound

HRID 2072772Notes

Reaction equation

HRID 2072772 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 (0.21 g, 0.15 ml) in dichloromethane (5 ml) was added dropwise, under nitrogen to a stirred, ice-cooled solution of 3-chloro-α-[[[1,1-dimethylethyl]amino]methyl]benzenemethanol (0.5 g) and triethylamine (0.38 g, 0.53 ml) in dichloromethane (40 ml). The reaction mixture was stirred at ambient temperature for 2 h., 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-62b96fd72cbe4a8a989cdfb80ff5ce4d
Source dataset
uspto-grants-1990_04
Patent number
US04914202

Reaction notes

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