Isopropanol → Propanamide, 3-mercapto-N-octyl-

HRID 974270Notes

Reaction equation

HRID 974270 reaction equation
C(O)(C)C.C[O:6][C:7](=O)[CH2:8][CH2:9][SH:10].[CH2:12]([NH2:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]>C(Cl)Cl>[CH2:12]([NH:20][C:7](=[O:6])[CH2:8][CH2:9][SH:10])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 8143OctylamineHCID 18050Methyl 3-mercaptopropionate

Product 1

HCID 11687178Propanamide, 3-mercapto-N-octyl-

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a small multi-necked reaction vessel equipped with a magnetic stirrer and gas inlet was placed isopropanol (2 ml), methyl-3-mercaptopropionate (2.0 g, 16.64 mmol), and n-octylamine (2.19 g, 16.94 mmol). The reaction vessel was connected to a trap containing bleach to trap mercaptan vapors, and the reaction was stirred for 19.5 hours while the reaction temperature was held at 30°-35° C. Methylene dichloride was added and the crude product was transferred to a round bottom flask. Evaporation of the solvent under reduced pressure yielded crude N-(n-octyl)-3-mercaptopropionamide as an oily white solid in essentially quantitative yield.

Workup

  1. customIn a small multi-necked reaction vessel equipped with a magnetic stirrer and gas inlet
  2. customThe reaction vessel was connected to a trap
  3. customwas held at 30°-35° C
  4. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-b1705aae89dc4e4c8af4a66ca165aa6e
Source dataset
uspto-grants-1991_11
Patent number
US05068338

Reaction notes

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