5-Chloro-2-methoxybenzene-1-sulfonyl chloride → N-(5-bromo-2-hydroxymethyl-phenyl)-5-chloro-2-methoxybenzenesulfonamide

HRID 1660857Notes

Reaction equation

HRID 1660857 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[CH2:9][OH:10].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([O:22][CH3:23])=[C:16]([S:18](Cl)(=[O:20])=[O:19])[CH:17]=1>N1C=CC=CC=1>[Br:8][C:6]1[CH:5]=[CH:4][C:3]([CH2:9][OH:10])=[C:2]([NH:1][S:18]([C:16]2[CH:17]=[C:12]([Cl:11])[CH:13]=[CH:14][C:15]=2[O:22][CH3:23])(=[O:19])=[O:20])[CH:7]=1

Participants

4

Reactant 2

HCID 27342725-Chloro-2-methoxybenzene-1-sulfonyl chlorideHCID 53440895(2-Amino-4-bromophenyl)methanol

Product 1

HCID 66789377N-(5-bromo-2-hydroxymethyl-phenyl)-5-chloro-2-methoxybenzenesulfonamideYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of (2-amino-4-bromo-phenyl)-methanol (1.53 g, 7.57 mmol) in pyridine (15 mL) was treated with 5-chloro-2-methoxybenzenesulfonyl chloride (1.85 g, 7.57 mmol) at room temperature and stirred for 72 h, then poured upon ice-cold 2 M aq. hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried (MgSO4), and evaporated to produce a gummy residue, from which the product was precipitated by addition of toluene. The precipitate was collected by filtration and dried to afford N-(5-bromo-2-hydroxymethyl-phenyl)-5-chloro-2-methoxy-benzenesulfonamide (2.51 g, 82%). Off-white solid, MS (ISP)=404.2 (M−H)−.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto produce a gummy residue
  6. customfrom which the product was precipitated by addition of toluene
  7. filtrationThe precipitate was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-8ecfda0949a747b7897e65f00a34f470
Source dataset
uspto-grants-2011_10
Patent number
US08030308B2

Reaction notes

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