4-Methoxybenzenesulfonyl chloride → HCID 3339285, compound

HRID 1059831Notes

Reaction equation

HRID 1059831 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11])[NH2:6].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22](Cl)(=[O:24])=[O:23])=[CH:18][CH:17]=1>N1C=CC=CC=1.C1COCC1>[CH3:14][O:15][C:16]1[CH:17]=[CH:18][C:19]([S:22]([NH:6][C:5]2[CH:7]=[C:8]([O:12][CH3:13])[C:9]([O:10][CH3:11])=[C:3]([O:2][CH3:1])[CH:4]=2)(=[O:24])=[O:23])=[CH:20][CH:21]=1

Participants

5

Reactant 2

HCID 74014-Methoxybenzenesulfonyl chlorideHCID 322853,4,5-Trimethoxyaniline

Product 1

HCID 3339285HCID 3339285, compoundYield 82.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,4,5-trimethoxyaniline (500 mg, 2.8 mmol) in pyridine (5 mL) was treated with 4-methoxybenzenesulfonyl chloride (564 mg, 2.8 mmol) in THF (5 mL), stirred at room temperature for 18 hours, concentrated, redissolved in THF (1 mL), treated with water with stirring, and filtered to provide 820 mg of the desired product.

Workup

  1. concentrationconcentrated
  2. dissolutionredissolved in THF (1 mL)
  3. additiontreated with water
  4. stirringwith stirring
  5. filtrationfiltered

Sources & evidence

ORD record
ord-899a1195e9ac4c7c9a8443155bb0c3fa
Source dataset
uspto-grants-2003_02
Patent number
US06521658B1

Reaction notes

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