Water → HCID 20536484, compound

HRID 1389085Notes

Reaction equation

HRID 1389085 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Br[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][CH3:27].O>CN(C)P(N(C)C)(N(C)C)=O>[F:1][C:2]1[CH:9]=[C:8]([NH:10][CH2:27][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][CH3:12])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 82131-BromohexadecaneHCID 27834134-Amino-2-fluorobenzonitrile

Product 1

HCID 20536484HCID 20536484, compound

Reagents, catalysts & solvents 1

HCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
120 °C

Procedure

2-Fluoro-4-aminobenzonitrile (11.8 g) and 1-bromohexadecane (15.3 g) are dissolved in hexamethylphosphoramide (200 ml.) and heated under an atmosphere of nitrogen in an oil bath maintained at 120° C. for 22 hours. The reaction mixture is cooled to room temperature and water is added gradually. The mixture is then chilled in an ice-bath and filtered. The solid is washed thoroughly with water and dried. The solid is recrystallized from ether-hexane to yield 2-fluoro-4-(hexadecylamino)benzonitrile as a pale yellow solid.

Workup

  1. temperatureheated under an atmosphere of 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. filtrationfiltered
  5. washThe solid is washed thoroughly with water
  6. customdried
  7. customThe solid is recrystallized from ether-hexane

Sources & evidence

ORD record
ord-b4a71311dfd4436bbbfcd142a0b2ee3f
Source dataset
uspto-grants-1981_01
Patent number
US04243609

Reaction notes

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