Water → HCID 20482491, compound

HRID 1389639Notes

Reaction equation

HRID 1389639 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][CH2:26][OH:27].O>CN(C)P(N(C)C)(N(C)C)=O>[OH:27][CH2:26][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][CH2:11][NH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 133964-AminobenzonitrileHCID 275701316-Bromo-1-hexadecanol

Product 1

HCID 20482491HCID 20482491, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
120 °C

Procedure

p-Aminobenzonitrile (12 g.) and 16-bromo-1-hexadecanol (15 g.) 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 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. The pale brownish yellow granular solid is obtained as a homogeneous product. Recrystallization from ether-hexane affords 4-(16-hydroxyhexadecylamino)benzonitrile as pale yellow prisms.

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. customThe pale brownish yellow granular solid is obtained as a homogeneous product
  11. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-66170c1e1e34473587952688d59b17a2
Source dataset
uspto-grants-1981_01
Patent number
US04245097

Reaction notes

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