2-Aminobenzyl alcohol → N-(2-(hydroxymethyl)phenyl)methanesulfonamide

HRID 58857

Reaction equation

HRID 58857 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][OH:14]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[OH:14][CH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[NH:6][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 2

HCID 214392-Aminobenzyl alcoholHCID 31297Methanesulfonyl chloride

Product 1

HCID 22955815N-(2-(hydroxymethyl)phenyl)methanesulfonamideYield 53.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent2×

Procedure

A solution of methane sulfonyl chloride (10.2 ml, 0.13 mol) in chloroform (100 mL) was added dropwise to a solution of (2-aminophenyl)methanol (15.0 g, 0.12 mol) in pyridine (100 mL) and chloroform (150 mL) under nitrogen over 1 h at 0° C. The reaction mixture was stirred for 12 h at ambient temperature and then washed with hydrochloric acid (2N, 200 ml×2). The organic phase was dried over anhydrous MgSO4 and concentrated. The residue was purified by flash column chromatography on silica gel (EtOAc/hexane=1:3) to afford N-[2-(hydroxymethyl)phenyl]methanesulfonamide (13.0 g, 53% yield) as a yellow oil.

Workup

  1. washwashed with hydrochloric acid (2N, 200 ml×2)
  2. dry with materialThe organic phase was dried over anhydrous MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by flash column chromatography on silica gel (EtOAc/hexane=1:3)

Sources & evidence

ORD record
ord-cc7c2c09648b42f9ab0908c369380260
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Linked notes

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