Hydrochloric Acid → N-{3-[(1-Chloro-2-nitroethenyl)sulfanyl]propyl}acetamide

HRID 371344Notes

Reaction equation

HRID 371344 reaction equation
[OH-].[Na+].[SH:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:10])[CH3:9].[Cl:11][C:12](Cl)=[CH:13][N+:14]([O-:16])=[O:15].Cl.[Cl-].[Na+]>CO>[Cl:11][C:12]([S:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:10])[CH3:9])=[CH:13][N+:14]([O-:16])=[O:15]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 122195711,1-Dichloro-2-nitroetheneHCID 20238484N-(3-Mercaptopropyl)acetamide

Product 1

HCID 53674132N-{3-[(1-Chloro-2-nitroethenyl)sulfanyl]propyl}acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

A solution of 0.12 g of sodium hydroxide in 5 ml of methanol was added over 10 minutes to a solution of 0.40 g of 1 in 5 ml of methanol. Then a solution of 0.95 g of 1,1-dichloro-2-nitroethene (13A) in 5 ml of methanol was added over 20 minutes, at 0° C. The mixture then was stirred for 20 minutes and poured into 2% hydrochloric acid saturated with sodium chloride. The resulting mixture was extracted with methylene chloride, the solvent was evaporated and the residue was purified over silica gel to give 13, as an oil.

Workup

  1. extractionThe resulting mixture was extracted with methylene chloride
  2. customthe solvent was evaporated
  3. customthe residue was purified over silica gel

Sources & evidence

ORD record
ord-1bcf7bbb274a4fd9b42c1a7daa22b0fd
Source dataset
uspto-grants-1985_07
Patent number
US04531002

Reaction notes

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