Triethylamine → N-(4'-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)propionamide

HRID 735186Notes

Reaction equation

HRID 735186 reaction equation
CS([Cl:5])(=O)=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:31])[CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29]O)=[CH:25][CH:24]=3)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.C(N(CC)CC)C>ClCCl>[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:31])[CH2:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([CH2:29][Cl:5])=[CH:25][CH:24]=3)=[CH:15][CH:14]=2)=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68816989N-(4'-chlorobiphenyl-4-yl)-3-(4-hydroxymethylphenyl)propionamide

Product 1

HCID 68815887N-(4'-chlorobiphenyl-4-yl)-3-(4-chloromethylphenyl)propionamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.43 mL (5.6 mmol) of methanesulfonic acid chloride is slowly added dropwise at ambient temperature to a solution of 2 g (5.47 mmol) of N-(4′-chlorobiphenyl-4-yl)-3-(4-hydroxymethylphenyl)propionamide and 1.56 mL (11.2 mmol) of triethylamine in 50 mL of dichloromethane and the reaction mixture is stirred for 24 hours at ambient temperature. It is extracted with water and the organic phase is dried over sodium sulfate. The solvent is distilled off and the residue is stirred with diisopropyl ether and suction filtered. Yield: 1.45 g (69% of theory); C22H19Cl2NO (M=384.3); calc.: molecular ion peak (M+H)+: 384/86/88 (Cl2) Found: molecular ion peak (M+H)+: 384/86/88 (Cl2); Rf value: 0.45 (silica gel, dichloromethane/ethanol (50:1)).

Workup

  1. extractionIt is extracted with water
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. distillationThe solvent is distilled off
  4. stirringthe residue is stirred with diisopropyl ether and suction
  5. filtrationfiltered

Sources & evidence

ORD record
ord-44bace9f7ca8488ea0a059dc5f9b07d3
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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