Iodine → HCID 178442143, compound

HRID 262357Notes

Reaction equation

HRID 262357 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24](=O)C)=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].II.[N:29]1C=CC=CC=1>>[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([C@H:12]2[CH2:17][CH2:16][C@H:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]#[N:29])=[CH:20][CH:19]=3)[CH2:14][CH2:13]2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

4

Reactant 3

HCID 807IodineHCID 1049PyridineHCID 178442142HCID 178442142, compound

Product 1

HCID 178442143HCID 178442143, compound

Procedure

14.0 g of trans-4-(4-n-pentylphenyl)-1-(4-acetylphenyl)-cyclohexane are heated for 2 hours on a steambath, together with 30 g of iodine and 100 ml of pyridine. After the evaporation of the pyridine under reduced pressure, the residue is dissolved in chloroform and purified over a short silica gel column. The eluate is evaporated and the 4-[trans-4-(4-n-pentylphenyl)-cyclohexyl]-benzoic acid remaining behind is brought to the boil for 2.5 hours with 30 ml of thionyl chloride. After distilling off the excess thionyl chloride, the 4-[trans-4-(4-n-pentylphenyl)-cyclohexyl]-benzoyl chloride is dissolved in 250 ml of dioxane and this solution mixed with 100 ml of 25% aqueous ammonia solution. The reaction mixture is poured into 1.5 liters of ice water and the precipitated 4-[trans-4-(4-n-pentylphenyl)-cyclohexyl]-benzamide filtered off and dried. The dry amide is dissolved at 40° in 170 ml of dimethyl formamide. To this solution are added dropwise at 50° , in the course of 30 minutes, 26 g of phosphorus oxide trichloride. After 1 hour the reaction mixture is poured into 300 ml of icewater. After extracting several times with 100 ml amounts of dichloromethane, washing of the extracts with 5% sodium bicarbonate solution and then with water, drying over sodium sulphate and evaporation, there is obtained trans-4-(4-n-pentylphenyl)-1-(4-cyanophenyl)-cyclohexane which is purified by recrystallisation from ethanol; m.p. 80°, c.p. 160°.

Workup

  1. customAfter the evaporation of the pyridine under reduced pressure
  2. dissolutionthe residue is dissolved in chloroform
  3. custompurified over a short silica gel column
  4. customThe eluate is evaporated
  5. distillationAfter distilling off the excess thionyl chloride
  6. dissolutionthe 4-[trans-4-(4-n-pentylphenyl)-cyclohexyl]-benzoyl chloride is dissolved in 250 ml of dioxane
  7. additionthis solution mixed with 100 ml of 25% aqueous ammonia solution
  8. additionThe reaction mixture is poured into 1.5 liters of ice water
  9. filtrationthe precipitated 4-[trans-4-(4-n-pentylphenyl)-cyclohexyl]-benzamide filtered off
  10. customdried
  11. dissolutionThe dry amide is dissolved at 40° in 170 ml of dimethyl formamide
  12. additionTo this solution are added dropwise at 50° , in the course of 30 minutes, 26 g of phosphorus oxide trichloride
  13. additionAfter 1 hour the reaction mixture is poured into 300 ml of icewater
  14. extractionAfter extracting several times with 100 ml amounts of dichloromethane
  15. washwashing of the extracts with 5% sodium bicarbonate solution
  16. dry with materialwith water, drying over sodium sulphate and evaporation

Sources & evidence

ORD record
ord-f54a6d13692145fd9135512be285129b
Source dataset
uspto-grants-1979_05
Patent number
US04154697

Reaction notes

Loading…