Thionyl Chloride → HCID 178456134, compound

HRID 1979962Notes

Reaction equation

HRID 1979962 reaction equation
[C:1]([C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1)#[N:2].S(Cl)([Cl:14])=O.CC1OC(C)O[CH:19]([CH3:24])O1>[Cl-].[Zn+2].[Cl-]>[C:1]([C@H:3]1[CH2:4][CH2:5][C@H:6]([C:9]([O:11][CH:19]([Cl:14])[CH3:24])=[O:10])[CH2:7][CH2:8]1)#[N:2]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 31264ParaldehydeHCID 178511260HCID 178511260, compound

Product 1

HCID 178456134HCID 178456134, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
90 °C

Procedure

trans-4-cyanocyclohexanecarboxylic acid (7.7 g; 0.05 mol) and thionyl chloride (8.0 g; 0.066 mol) was mixed and refluxed for 30 min. Excess thionyl chloride was evaporated in vacuum. Paraldehyde (2.5 g; 0.062 mol) and a catalytic amount of zinc chloride were added and the mixture was heated at 90° C. for 11/2 h with stirring. The cooled mixture was extracted with ether, washed with sodium bicarbonate solution, dried and evaporated, the product was distilled at 112° C./1 Pa. Yield 6.5 g of an oil.

Workup

  1. temperaturerefluxed for 30 min
  2. customExcess thionyl chloride was evaporated in vacuum
  3. extractionThe cooled mixture was extracted with ether
  4. washwashed with sodium bicarbonate solution
  5. customdried
  6. customevaporated
  7. distillationthe product was distilled at 112° C./1 Pa

Sources & evidence

ORD record
ord-a1a67fbbe0ec4259a7575c8a2ea8e56f
Source dataset
uspto-grants-1984_11
Patent number
US04483867

Reaction notes

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