5-Amino-2-methoxyphenol → 1-[(3-Hydroxy-4-methoxyphenyl)aminosulfonyl]-3,4,5-trimethoxybenzene

HRID 635996Notes

Reaction equation

HRID 635996 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:13](Cl)(=[O:15])=[O:14])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[OH:17][C:18]1[CH:19]=[C:20]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[NH2:21]>CO>[OH:17][C:18]1[CH:19]=[C:20]([NH:21][S:13]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=2)(=[O:15])=[O:14])[CH:22]=[CH:23][C:24]=1[O:25][CH3:26]

Participants

4

Reactant 2

HCID 743145-Amino-2-methoxyphenolHCID 151961583,4,5-Trimethoxybenzene-1-sulfonyl chloride

Product 1

HCID 98422591-[(3-Hydroxy-4-methoxyphenyl)aminosulfonyl]-3,4,5-trimethoxybenzeneYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3,4,5-trimethoxybenzenesulfonyl chloride (500 mg, 1.88 mmol) in methanol (10 mL) was added 3-hydroxy4-methoxyaniline (523 mg, 3.76 mmol) at ambient temperature. After stirring for 1 h, the reaction mixture was concentrated and the crude residue was purified by chromatography over silica to afford 430 mg (62%) of product as fme white needles, m.p. 145-146° C. 1H—NMR (CDCl3): δ9.74 (1H, s), 9.15 (1H, s), 6.98 (2H, s), 6.78 (1H, d, J=8.8 Hz), 6.63 (1H, d, J=2.6 Hz), 6.50 (1H, dd, J=8.8, 2.6 Hz), 3.76 (6H, s), 3.70 (3H, s), 3.68 (3H, s). Anal. Calcd. for C16H19N1O7S: C, 52.03; H, 5.18; N, 3.79; S, 8.68. Found: C, 51.87; H, 5.28; N, 3.76; S, 8.77.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe crude residue was purified by chromatography over silica

Sources & evidence

ORD record
ord-a2141658295a4a09878cc8e56b580e14
Source dataset
uspto-grants-2001_02
Patent number
US06191170B1

Reaction notes

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