HCID 20525748, compound → HCID 20525739, compound

HRID 1702691Notes

Reaction equation

HRID 1702691 reaction equation
[CH2:1]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]([NH2:27])=O)=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>C1C=CC=CC=1>[CH2:1]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]#[N:27])=[CH:20][CH:19]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 1

HCID 20525748HCID 20525748, compound

Product 1

HCID 20525739HCID 20525739, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 2-(4-hexadecylaminophenyl)acetamide in benzene is cooled to 10° and a stream of dry hydrogen chloride gas is bubbled in. After one-half hour an excess of thionyl chloride is added and the reaction is heated to reflux for five hours. The reaction is then cooled in ice and poured into a slurry of ice and water. Cold 50% aqueous potassium hydroxide is slowly added until the mixture is basic to litmus. The layers are then separated and the aqueous portion is extracted with more benzene. The combined benzene extracts are washed with aqueous sodium carbonate and then with water. Evaporation of the solvent and recrystallization of the residue from hexane gives (4-hexadecylaminophenyl)acetonitrile.

Workup

  1. customa stream of dry hydrogen chloride gas is bubbled in
  2. additionAfter one-half hour an excess of thionyl chloride is added
  3. temperaturethe reaction is heated
  4. temperatureto reflux for five hours
  5. temperatureThe reaction is then cooled in ice
  6. additionpoured into a slurry of ice and water
  7. additionCold 50% aqueous potassium hydroxide is slowly added until the mixture
  8. customThe layers are then separated
  9. extractionthe aqueous portion is extracted with more benzene
  10. washThe combined benzene extracts are washed with aqueous sodium carbonate
  11. customEvaporation of the solvent and recrystallization of the residue from hexane

Sources & evidence

ORD record
ord-faeb5030b9ec4b46a0398de24d958d17
Source dataset
uspto-grants-1982_09
Patent number
US04348399

Reaction notes

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