Water → HCID 13019275, compound
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
Product 1
Reagents, catalysts & solvents 1
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 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 14.2 g. of pale brownish yellow granular solid is obtained as a homogeneous product. Recrystallization from ether-hexane affords p-hexadecylaminobenzonitrile as a pale yellow prisms, m.p. 63°-64° C.
Workup
- temperatureheated under nitrogen in an oil bath
- temperatureThe reaction mixture is cooled to room temperature
- temperatureThe mixture is then chilled in an ice-bath
- customThe precipitate separated
- filtrationis filtered
- washwashed thoroughly with water
- customdried
- washIt is then washed repeatedly with hexane
- customdried
- customof pale brownish yellow granular solid is obtained as a homogeneous product
- customRecrystallization from ether-hexane
Sources & evidence
- ORD record
- ord-f073b798d2bb4715ba9e9c407a8b5e9f
- Source dataset
- uspto-grants-1981_06
- Patent number
- US04273785
Reaction notes
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