Hydrochloric Acid → 3,4,5-Trimethoxybenzene-1-sulfonyl chloride

HRID 635994Notes

Reaction equation

HRID 635994 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])N.N([O-])=O.[Na+].[S:18](=[O:20])=[O:19].O.[ClH:22]>NC1C=CC=CC=1.C(O)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([S:18]([Cl:22])(=[O:20])=[O:19])[CH:7]=[C:8]([O:12][CH3:13])[C:9]=1[O:10][CH3:11]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 1119Sulfur DioxideHCID 322853,4,5-TrimethoxyanilineHCID 23668193Sodium Nitrite

Product 1

HCID 151961583,4,5-Trimethoxybenzene-1-sulfonyl chloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6115AnilineSolvent

Procedure

3,4,5-Trimethoxybenzenesulfonyl chloride was synthesized from 3,4,5-trimethoxyaniline according to the procedure described in G. Pifferi and R. Monguzzi, Journal of Pharmaceutical Sciences, 1973, 62, 1393. In this procedure the aniline was dissolved in concentrated hydrochloric acid and to the resulting mixture was added a solution of aqueous sodium nitrite at 0° C., the resulting mixture containing the desired diazonium salt was added at 5° C. to a saturated solution of sulfur dioxide in glacial acetic acid containing substoichiometric amount of cuprous chloride. The mixture was stirred at ambient temperature for 3h, poured into cold water, and the product extracted with dichloromethane. The solvent was evaporated and the solid residue was recrystallized from hexanes.

Workup

  1. extractionthe product extracted with dichloromethane
  2. customThe solvent was evaporated
  3. customthe solid residue was recrystallized from hexanes

Sources & evidence

ORD record
ord-67b2e482414a4ede89547c7327cd560f
Source dataset
uspto-grants-2001_02
Patent number
US06191170B1

Reaction notes

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