1-Octadecanethiol → HCID 20393260, compound

HRID 1863039Notes

Reaction equation

HRID 1863039 reaction equation
[CH2:1]([SH:19])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:20]/[CH:21]=[CH:22]/[C:23]#[N:24]>C(Cl)Cl.C[O-].[Na+]>[CH2:1]([S:19][CH:21]([CH3:20])[CH2:22][C:23]#[N:24])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 2

HCID 179051-OctadecanethiolHCID 637921Crotononitrile

Product 1

HCID 20393260HCID 20393260, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 10942334Sodium MethoxideCatalystHCID 6344DichloromethaneSolvent

Procedure

Preparation of ##STR42## Sodiummethoxide (100 mg) was suspended in stearyl mercaptan (57.2 g, 0.2 mol). Crotonitril (16.8 g, 0.25 mol) was added dropwise under N2 -atmosphere at 50° C. After 12 hours the reaction solution was taken up in methylene chloride. The solution was washed with 2 n sulfuric acid and with water, dried and the solvent removed under vacuum. The resulting crystalline mass was recrystallized from ethanol to give 56.5 g, 80% yield of 3-(stearylmercapto)-butyronitrile, melting at 38° C.

Workup

  1. washThe solution was washed with 2 n sulfuric acid and with water
  2. customdried
  3. customthe solvent removed under vacuum
  4. customThe resulting crystalline mass was recrystallized from ethanol

Sources & evidence

ORD record
ord-290e70639f204144a97e01414006735a
Source dataset
uspto-grants-1979_09
Patent number
US04167618

Reaction notes

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