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

HRID 2228436Notes

Reaction equation

HRID 2228436 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 fine white needles, m.p. 145-146° C. 1H-NMR (CDCl3): δ 9.74 (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. Each of the phenols above, as well as the related members having different substitution patterns can be phosphorylated using known methods including the procedure described in detail in Example 1.

Workup

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

Sources & evidence

ORD record
ord-81a7d6bcd3454f5fbd90ef260354094d
Source dataset
uspto-grants-2002_07
Patent number
US06417176B2

Reaction notes

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