1-Octanethiol → 4-(Octylsulfanyl)benzonitrile

HRID 1742766Notes

Reaction equation

HRID 1742766 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:16]([SH:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>CC(N(C)C)=O>[CH2:16]([S:24][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 81441-OctanethiolHCID 11430Potassium CarbonateHCID 121634-Chlorobenzonitrile

Product 1

HCID 151853024-(Octylsulfanyl)benzonitrileYield 104.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

103.2 g (0.75 mol) of p-chlorobenzonitrile, 140 g of potassium carbonate and 143.2 ml (0.825 mol) of octanethiol in dimethylacetamide are stirred at 100° C. for about 16 hours in a sulfonation flask under a protective-gas atmosphere. The white suspension obtained is cooled, poured into ice water and extracted a number of times with dichloromethane. The organic phases are combined, washed with water, dried over MgSO4, filtered and evaporated, giving 193.1 g of crude product, which is distilled at 92° C./0.1 mm Hg.

Workup

  1. customThe white suspension obtained
  2. temperatureis cooled
  3. extractionextracted a number of times with dichloromethane
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-c0f6dbcd024d4c73834991e1b3280831
Source dataset
uspto-grants-1994_08
Patent number
US05340701

Reaction notes

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