Hydrochloric Acid → N-Cyclohexyl-3-sulfanylpropanamide

HRID 1608002Notes

Reaction equation

HRID 1608002 reaction equation
[C:1](=[S:3])=S.[S-2].[Na+].[Na+].[CH:7]1([NH:13][C:14](=[O:17])[CH:15]=C)[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Cl>CO.O>[CH:7]1([NH:13][C:14](=[O:17])[CH2:15][CH2:1][SH:3])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6348Carbon DisulfideHCID 14804Sodium SulfideHCID 137811Acrylamide, N-cyclohexyl-

Product 1

HCID 14618019N-Cyclohexyl-3-sulfanylpropanamideYield 100.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Carbon disulfide (76 g) was added to a mixture of sodium sulfide (55 g) in methanol (80 g) and water (80 g) and kept at 20° C. To this was slowly added N-cyclohexylacrylamide (100 g) maintaining the pot temperature at 20°-30° C. The resulting solution was stirred for an additional 2-3 hour and neutralized with concentrated hydrochloric acid. The organic layer was separated, washed with water and evaporated to dryness to afford 122.6 g of N-cyclohexyl-3-mercaptopropionamide (90.5% yield).

Workup

  1. customkept at 20° C
  2. temperaturemaintaining the pot temperature at 20°-30° C
  3. customThe organic layer was separated
  4. washwashed with water
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-8ee75b997d6f40e9a3e1de5fa2a94c51
Source dataset
uspto-grants-1989_09
Patent number
US04868310

Reaction notes

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