Dimethyl Sulfoxide → HCID 178447873, compound

HRID 1589741Notes

Reaction equation

HRID 1589741 reaction equation
[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:17]=[CH:16][C:13]([CH2:14]Cl)=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[C-:18]#[N:19].[Na+].CS(C)=O>O>[CH2:1]([C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:17]=[CH:16][C:13]([CH2:14][C:18]#[N:19])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 178447872HCID 178447872, compound

Product 1

HCID 178447873HCID 178447873, compoundYield 97.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

114 g (0.45 mol) of 4-(trans-4'-propylcyclohexyl) benzyl chloride, 27 g (0.55 mol) of NaCN and 113 cm3 of DMSO were mixed and while stirring, the mixture was heated to a temperature of 140° C. by a mantle heater. The product of the reaction was cooled to room temperature. 400 cm3 of water was added and extracted three times with 100 cm3 of chloroform. The chloroform layers were combined and washed with 10% hydrochloric acid and water. The chloroform was distilled off under reduced pressure and the residue was distilled under reduced pressure (155° C./2.5 mmHg) to yield 106 g (0.44 mol) of 4-(trans-4'-propylcyclohexyl) benzyl cyanide.

Workup

  1. temperatureThe product of the reaction was cooled to room temperature
  2. extractionextracted three times with 100 cm3 of chloroform
  3. washwashed with 10% hydrochloric acid and water
  4. distillationThe chloroform was distilled off under reduced pressure
  5. distillationthe residue was distilled under reduced pressure (155° C./2.5 mmHg)

Sources & evidence

ORD record
ord-10e32e9391c348b9b5456c67b7bd452d
Source dataset
uspto-grants-1993_04
Patent number
US05200110

Reaction notes

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