Water → HCID 13019275, compound

HRID 2049848Notes

Reaction equation

HRID 2049848 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

Conditions

Temperature
120 °C

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° C. for 22 hours. The reaction mixture is cooled to room-temperature, and water (50 ml.) is added gradually. The mixtue 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, providing 14.2 g. of a pale brownish yellow granular solid as a homogeneous product. Recrystallization from ether-hexane affords p-hexadecylaminobenzonitrile as pale yellow prisms, m.p. 63°-64° C.

Workup

  1. temperatureheated under nitrogen in an oil bath
  2. additionis added gradually
  3. temperatureThe mixtue 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. customproviding 14.2 g
  11. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-05e3c32b73e3428db91799f9e8195049
Source dataset
uspto-grants-1980_04
Patent number
US04198522

Reaction notes

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