Methanesulfonyl chloride → HCID 67599725, compound

HRID 1417328Notes

Reaction equation

HRID 1417328 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][S:16][C:17]2[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>N1C=CC=CC=1>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][S:16][C:17]2[CH:18]=[CH:19][C:20]([NH:23][S:25]([CH3:24])(=[O:27])=[O:26])=[CH:21][CH:22]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 67598789HCID 67598789, compound

Product 1

HCID 67599725HCID 67599725, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2.4 g of 4-methyl-N-[4-(4-aminophenylthio)butyl]benzenesulfonamide (Example 72) in 50 ml of pyridine is treated with 1.05 g of methane-sulfonyl chloride, and the solution stirred and heated on the steam bath for 6 hours. The pyridine is then removed in vacuo. The residue is shaken with 100 ml of water, and the mixture acidified below pH=2 with concentrated hydrochloric acid. The precipitate is collected, washed with water and dried. Recrystallization from 50% aqueous ethanol gives shiny white crystals after drying, m.p. 95°-96° C.; yield, 1.2 g.

Workup

  1. temperatureheated on the steam bath for 6 hours
  2. customThe pyridine is then removed in vacuo
  3. stirringThe residue is shaken with 100 ml of water
  4. customThe precipitate is collected
  5. washwashed with water
  6. customdried
  7. customRecrystallization from 50% aqueous ethanol
  8. customgives shiny white crystals
  9. customafter drying
  10. customyield

Sources & evidence

ORD record
ord-b2653b8caa8149dabef2443070eef79f
Source dataset
uspto-grants-1999_03
Patent number
US05877196

Reaction notes

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