Methanesulfonyl chloride → N-(3-(chloromethyl)phenyl)acetamide

HRID 912528Notes

Reaction equation

HRID 912528 reaction equation
CS([Cl:5])(=O)=O.[C:6]([NH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH2:13]O)(=[O:8])[CH3:7]>C(Cl)Cl.CCOC(C)=O.CO>[C:6]([NH:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH2:13][Cl:5])(=[O:8])[CH3:7]

Participants

6

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 966393-Acetaminobenzyl alcohol

Product 1

HCID 18792834N-(3-(chloromethyl)phenyl)acetamide

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Methanesulphonyl chloride (0.15 ml) was added to a stirred solution of 3-acetylaminobenzylalcohol (260 mg) and TEA (0.26 ml) in DCM (2 ml) at 0° C. The reaction was allowed to warm to room temperature and stirred for two hours. The mixture was diluted with EtOAc (20 mL) and MeOH (1 ml) and stirred for 5 minutes. The mixture was then washed with water (30 ml), organic layer was dried over sodium sulphate and solvent evaporated. The residue was columned on silica gel using DCM then ethyl acetate as eluant to give 3-acetylaminobenzylchloride (210 mg). 1H NMR (CDCl3) δ: 7.59 (s, 1H), 7.41 (d, 1H), 7.31 (t, 1H), 7.14 (d, 1H), 4.56 (s, 2H), 2.18 (s, 3H).

Workup

  1. stirringstirred for 5 minutes
  2. washThe mixture was then washed with water (30 ml), organic layer
  3. dry with materialwas dried over sodium sulphate and solvent
  4. customevaporated

Sources & evidence

ORD record
ord-82ac92edd41c47bfb74e0bfbaae9f6ba
Source dataset
uspto-grants-2011_09
Patent number
US08026236B2

Reaction notes

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