3,4-Dimethoxybenzenesulfonyl chloride → N-{4-chloro-2-[(3-methoxyphenyl)(hydroxy)methyl]phenyl}-3,4-dimethoxybenzenesulfonamide

HRID 747600Notes

Reaction equation

HRID 747600 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[CH:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)[OH:10].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([S:29](Cl)(=[O:31])=[O:30])[CH:24]=[CH:25][C:26]=1[O:27][CH3:28]>N1C=CC=CC=1.C(OCC)(=O)C>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][S:29]([C:23]2[CH:24]=[CH:25][C:26]([O:27][CH3:28])=[C:21]([O:20][CH3:19])[CH:22]=2)(=[O:31])=[O:30])=[C:3]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[OH:10])[CH:4]=1

Participants

5

Reactant 2

HCID 27341833,4-Dimethoxybenzenesulfonyl chlorideHCID 57777837(2-Amino-5-chlorophenyl)(3-methoxyphenyl)methanol

Product 1

HCID 68567514N-{4-chloro-2-[(3-methoxyphenyl)(hydroxy)methyl]phenyl}-3,4-dimethoxybenzenesulfonamideYield 93.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 1 g of (2-amino-5-chlorophenyl)(3-methoxyphenyl)methanol dissolved in 6 ml of pyridine are added, at room temperature, 1.08 g of 3,4-dimethoxybenzenesulfonyl chloride. After 18 hours, the reaction medium is taken up in ethyl acetate and washed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with dichloromethane to give 1.65 g of the expected product.

Workup

  1. additionare added, at room temperature
  2. washwashed with water
  3. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is chromatographed on a column of silica gel
  6. washeluting with dichloromethane

Sources & evidence

ORD record
ord-3654c2a01f984d1f8949786676da6b61
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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