Water → 3,4-dichlorobenzenesulfonamide

HRID 1377788Notes

Reaction equation

HRID 1377788 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].[NH2:13]CC1C2SC3C(=CC=CC=3)C(=O)C=2C(NCCN(CC)CC)=CC=1.O.[OH-].[Na+]>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH2:13])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 7383Benzenesulfonyl chloride, 3,4-dichloro-HCID 14798Sodium HydroxideHCID 9998338HCID 9998338, compound

Product 1

HCID 2330973,4-dichlorobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3,4-dichlorobenzenesulfonyl chloride (1.84 g, 7.5 mmol) in 35 mL of dry pyridine was added 2.5 g (7 mmol) of 4-(aminomethyl)-1-[[2-(diethylamino)ethyl]amino]-thioxanthen-9-one (prepared by the method described in Example 4) under nitrogen and the reaction mixture was stirred at room temperature for 15 min. and then was allowed to stand for approximately 72 hours. The reaction mixture was poured into 75 mL of water containing 0.75 g of NaOH, and extracted into chloroform. The organic layer was washed with water (2x) and brine, and dried over sodium sulfate. Chloroform was removed in vacuo, the residue was recrystallized from ethanol to afford 1.24 g of N-[[1-[[2-(diethylamino)]ethyl]amino]-9-oxothioxanthen-4-yl]methyl]-3,4-dichlorobenzenesulfonamide, m.p. 95° C. (dec.). The free base was dissolved in methanol and treated with methanesulfonic acid in methanol to afford the methanesulfonate·1/2 hydrate, m.p. 55° C. (dec.).

Workup

  1. customprepared by the method
  2. waitto stand for approximately 72 hours
  3. extractionextracted into chloroform
  4. washThe organic layer was washed with water (2x) and brine
  5. dry with materialdried over sodium sulfate
  6. customChloroform was removed in vacuo
  7. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-e8c0ff2f075d4d62baadcaf9f1cc6285
Source dataset
uspto-grants-1997_09
Patent number
US05665760

Reaction notes

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