N-(4-Chloro-2-(2-chlorobenzoyl)phenyl)-3,4-dimethoxybenzenesulfonamide → N-{4-chloro-2-[(2-chlorophenyl)(hydroxy)methyl]phenyl}-3,4-dimethoxybenzenesulfonamide

HRID 747592Notes

Reaction equation

HRID 747592 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)(=[O:11])=[O:10])=[C:4]([C:22](=[O:30])[C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[CH:3]=1.[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=2)(=[O:10])=[O:11])=[C:4]([CH:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[Cl:29])[OH:30])[CH:3]=1

Participants

4

Reactant 2

HCID 985426N-(4-Chloro-2-(2-chlorobenzoyl)phenyl)-3,4-dimethoxybenzenesulfonamideHCID 4311764Sodium borohydride

Product 1

HCID 68566152N-{4-chloro-2-[(2-chlorophenyl)(hydroxy)methyl]phenyl}-3,4-dimethoxybenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

16 g of N-[4-chloro-2-(2-chlorobenzoyl)phenyl]-3,4-dimethoxybenzenesulfonamide dissolved in 900 ml of ethanol are added portionwise 3.93 g of sodium borohydride, and the mixture is left for 18 hours at room temperature. The reaction medium is concentrated and the residue is taken up in ethyl acetate and washed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is solidified with diisopropyl ether; after filtering off and drying the precipitate, 14.66 g of the expected product are obtained.

Workup

  1. concentrationThe reaction medium is concentrated
  2. washwashed with water
  3. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. filtrationafter filtering off
  6. dry with materialdrying the precipitate, 14.66 g of the expected product
  7. customare obtained

Sources & evidence

ORD record
ord-ac9497edd06a474a914d840599309e93
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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