Hydrochloric Acid → N-(3-(1-Chloro-2-nitroethenylthio)propyl)benzenesulfonamide

HRID 364861Notes

Reaction equation

HRID 364861 reaction equation
[OH-].[Na+].[SH:3][CH2:4][CH2:5][CH2:6][NH:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9].[Cl:17][C:18](Cl)=[CH:19][N+:20]([O-:22])=[O:21].Cl.[Cl-].[Na+]>CO>[Cl:17][C:18]([S:3][CH2:4][CH2:5][CH2:6][NH:7][S:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:10])=[O:9])=[CH:19][N+:20]([O-:22])=[O:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 122195711,1-Dichloro-2-nitroetheneHCID 20238482N-(3-Mercaptopropyl)benzenesulfonamide

Product 1

HCID 54130017N-(3-(1-Chloro-2-nitroethenylthio)propyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of 0.08 g of sodium hydroxide in 3 ml of methanol was added drop-by-drop over 5 minutes to a solution of 0.23 g of 3 in 5 ml of methanol. The resulting mixture was added drop-by-drop over 20 minutes to a solution of 0.28 g of 13A in 6 ml of methanol at 0° C. The mixture was held at 0° C. for 30 minutes, then poured into 2% hydrochloric acid saturated with sodium chloride. The resulting mixture was extracted with methylene chloride, the solvent was evaporated from the extract and the residue was chromatographed over silica gel to give 14, as a solid, m.p.: 105°-106° C.

Workup

  1. extractionThe resulting mixture was extracted with methylene chloride
  2. customthe solvent was evaporated from the
  3. extractionextract
  4. customthe residue was chromatographed over silica gel

Sources & evidence

ORD record
ord-0f69d14c4db346b98b08abc54d58fad2
Source dataset
uspto-grants-1986_08
Patent number
US04606862

Reaction notes

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