Hexamethylphosphoramide → 4-(15-Carbomethoxypentadecylamino)benzonitrile

HRID 1278390Notes

Reaction equation

HRID 1278390 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][C:26]([O:28][CH3:29])=[O:27].CN(C)P(N(C)C)(N(C)C)=O>O>[C: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)([O:28][CH3:29])=[O:27]

Participants

5

Reactant 3

HCID 12679HexamethylphosphoramideHCID 133964-AminobenzonitrileHCID 2736822Methyl 16-bromohexadecanoate

Product 1

HCID 211633764-(15-Carbomethoxypentadecylamino)benzonitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 12 g. of 4-aminobenzonitrile and 15 g. of methyl 16-bromohexadecanoate in 200 ml. of hexamethylphosphoramide is heated at 120° for 22 hours, allowed to cool, and diluted with water. The mixture is chilled and the precipitate which forms is collected, dried, and recrystallized from etherhexane to yield 4-(15-carbomethoxypentadecylamino)benzonitrile as a white solid.

Workup

  1. temperatureto cool
  2. temperatureThe mixture is chilled
  3. customthe precipitate which forms is collected
  4. customdried
  5. customrecrystallized from etherhexane

Sources & evidence

ORD record
ord-a79f99236ffc4254a46d6ef16485faa9
Source dataset
uspto-grants-1981_07
Patent number
US04281018

Reaction notes

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