Water → HCID 20331289, compound

HRID 2057658Notes

Reaction equation

HRID 2057658 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]Br)=[CH:14][CH:13]=1.O>CN(C)P(N(C)C)(N(C)C)=O>[CH3:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][NH:1][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 133964-AminobenzonitrileHCID 21837968HCID 21837968, compound

Product 1

HCID 20331289HCID 20331289, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
120 °C

Procedure

4-Aminobenzonitrile (11.8 g.) and 10-(4-methoxyphenyl)decylbromide (16.3 g.) are dissolved in hexamethylphosphoramide (100 ml.) and heated under nitrogen in an oil bath maintained at 120° C. for 22 hours. The reaction mixture is cooled to room temperature and water (100 ml.) is added gradually. The mixture is then chilled in an ice bath. The precipitate separated is filtered, washed thoroughly with water, and dried. It is then washed repeatedly with hexane and dried. Recrystallization from ether-hexane affords 4-[10-(4-methoxyphenyl)decylamino]benzonitrile as pale yellow crystals.

Workup

  1. temperatureheated under nitrogen in an oil bath
  2. temperatureThe reaction mixture is cooled to room temperature
  3. temperatureThe mixture is then chilled in an ice bath
  4. customThe precipitate separated
  5. filtrationis filtered
  6. washwashed thoroughly with water
  7. customdried
  8. washIt is then washed repeatedly with hexane
  9. customdried
  10. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-99c84823c36043d9a6796df4b037a2eb
Source dataset
uspto-grants-1980_07
Patent number
US04211783

Reaction notes

Loading…