Water → HCID 21838829, compound

HRID 1740518Notes

Reaction equation

HRID 1740518 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:28])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].O>CN(C)C(=O)C>[CH2:16]([S:28][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][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 81951-DodecanethiolHCID 11430Potassium CarbonateHCID 121634-Chlorobenzonitrile

Product 1

HCID 21838829HCID 21838829, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A suspension consisting of 75.66 g (0.55 mol) of 4-chlorobenzonitrile, 106.42 g (0.77 mol) of potassium carbonate and 111.32 g (0.55 mol) of 1-dodecanethiol is heated, with stirring, under an inert gas atmosphere in 280 ml of N,N-dimethylacetamide to 130° C. and is then stirred at this temperature for 24 hours. After cooling the reaction mixture to room temperature, it is poured on a mixture of 700 g of ice and 750 ml of water. The mixture is filtered and the filter cake is washed with water. The product is recrystallised from methanol and dried at 50° C. under vacuum, affording 160.2 g (96% of theory) of 4-(dodecyl-thio)benzonitrile.

Workup

  1. temperatureis heated
  2. filtrationThe mixture is filtered
  3. washthe filter cake is washed with water
  4. customThe product is recrystallised from methanol
  5. customdried at 50° C. under vacuum

Sources & evidence

ORD record
ord-07446302bc404a20be01c0081ab54b4a
Source dataset
uspto-grants-1999_10
Patent number
US05969154

Reaction notes

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