Water → Ethyl 7-{[4-(acetyloxy)nonyl](cyano)amino}heptanoate

HRID 1729911Notes

Reaction equation

HRID 1729911 reaction equation
[H-].[Na+].[NH:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:4]#[N:5].Cl[CH2:18][CH2:19][CH2:20][CH:21]([O:27][C:28](=[O:30])[CH3:29])[CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].O>C1C=CC=CC=1.CN(C)C=O>[C:28]([O:27][CH:21]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:20][CH2:19][CH2:18][N:3]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:4]#[N:5])(=[O:30])[CH3:29]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 131047161-Chloro-4-acetoxynonaneHCID 21501476Ethyl 7-(cyanoamino)heptanoate

Product 1

HCID 71444712Ethyl 7-{[4-(acetyloxy)nonyl](cyano)amino}heptanoate

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (57%, in mineral oil) (0.48 g., 0.01 mole) is washed twice with benzene then suspended in benzene (50 ml.) and dimethylformamide (50 ml.). Ethyl 7-cyanamidoheptanoate (1.98 g. 0.01 mole) (Example N, Step 2) is added and the suspension heated on the steam bath for 15 minutes. The reaction mixture is cooled to room temperature, 1-chloro-4-acetoxynonane (2.6 g., 0.01 mole) (Example A, Step 3) is added and then the reaction is heated on the steam bath for 2 hours then stirred 18 hours at room temperature. The reaction is poured into water (300 ml.) and extracted with benzene (3 × 100 ml.). The benzene is washed with brine then dried over sodium sulfate. Removal of the solvent yields an oil which is purified by silica gel chromatography, elution solvent 3% methanol in chloroform, evaporation of the appropriate fraction affords ethyl 7-[N-(4-acetoxynonyl) cyanamido]-heptanoate. The yield is 3.2 g. (83 %).

Workup

  1. temperaturethe suspension heated on the steam bath for 15 minutes
  2. temperaturethe reaction is heated on the steam bath for 2 hours
  3. extractionextracted with benzene (3 × 100 ml.)
  4. washThe benzene is washed with brine
  5. dry with materialthen dried over sodium sulfate
  6. customRemoval of the solvent
  7. customyields an oil which
  8. customis purified by silica gel chromatography, elution solvent 3% methanol in chloroform, evaporation of the appropriate fraction

Sources & evidence

ORD record
ord-7f39267595ec464295f68f56c928d005
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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