Water → HCID 13019275, compound

HRID 1855823Notes

Reaction equation

HRID 1855823 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.Br[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O>CN(C)P(N(C)C)(N(C)C)=O>[CH2:26]([NH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH3:11]

Participants

5

Reactant 3

HCID 962WaterHCID 82131-BromohexadecaneHCID 133964-Aminobenzonitrile

Product 1

HCID 13019275HCID 13019275, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Procedure

p-Aminobenzonitrile (11.8 g., 0.1 mole) and 1-bromohexadecane (15.25 g., 0.05 mole) are dissolved in hexamethylphosphoramide (200 ml.) and heated under nitrogen in an oil-bath maintained at 120° for 22 hours. The reaction mixture is cooled to room temperature and water (50 ml.) is added gradually. The mixture is then chilled in an ice-bath. The precipitate is filtered, washed thoroughly with water and dried. It is then washed repeatedly with hexane and dried; 14.2 g. pale brownish yellow granular solid is obtained as homogeneous product. Crystallization from ether-hexane affords pale yellow prisms, melting point 63°-64° C.

Workup

  1. temperatureheated under nitrogen in an oil-bath
  2. temperaturemaintained at 120° for 22 hours
  3. temperatureThe mixture is then chilled in an ice-bath
  4. filtrationThe precipitate is filtered
  5. washwashed thoroughly with water
  6. customdried
  7. washIt is then washed repeatedly with hexane
  8. customdried
  9. custompale brownish yellow granular solid is obtained as homogeneous product
  10. customCrystallization from ether-hexane
  11. customaffords pale yellow prisms, melting point 63°-64° C.

Sources & evidence

ORD record
ord-d55385aa085f45808a5d27a0e5ba147f
Source dataset
uspto-grants-1980_08
Patent number
US04216330

Reaction notes

Loading…