3,4-Dimethoxybenzenesulfonyl chloride → N-(2-chloro-5-hydroxymethyl-phenyl)-3,4-dimethoxy-benzenesulfonamide

HRID 1674627Notes

Reaction equation

HRID 1674627 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:9][OH:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([S:21](Cl)(=[O:23])=[O:22])[CH:16]=[CH:17][C:18]=1[O:19][CH3:20]>N1C=CC=CC=1>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:9][OH:10])=[CH:3][C:2]=1[NH:1][S:21]([C:15]1[CH:16]=[CH:17][C:18]([O:19][CH3:20])=[C:13]([O:12][CH3:11])[CH:14]=1)(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 13636475(3-Amino-4-chlorophenyl)methanol

Product 1

HCID 57511303N-(2-chloro-5-hydroxymethyl-phenyl)-3,4-dimethoxy-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (3-amino-4-chloro-phenyl)-methanol (2.0 g, 12.7 mmol) in pyridine (26 mL) was treated with 3,4-dimethoxybenzenesulfonyl chloride (3.3 g, 1.1 eq). The solution was stirred at RT overnight. The mixture was then partitioned between EA and 3M HCl. The organic layer was washed with brine, dried over MgSO4 and concentrated. The product was recovered as a brownish foam.

Workup

  1. customThe mixture was then partitioned between EA and 3M HCl
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe product was recovered as a brownish foam

Sources & evidence

ORD record
ord-2ca004509b7442898c7610746b030470
Source dataset
uspto-grants-2011_08
Patent number
US08003654B2

Reaction notes

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