Water → HCID 86734144, compound

HRID 1729916Notes

Reaction equation

HRID 1729916 reaction equation
[H-].[Na+].[C:3]([O:6][CH:7]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:8][CH2:9][CH2:10][NH:11][C:12]#[N:13])(=[O:5])[CH3:4].Br[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([CH3:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27].O>C1C=CC=CC=1>[C:3]([O:6][CH:7]([CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:8][CH2:9][CH2:10][N:11]([CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH:25]([CH3:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:12]#[N:13])(=[O:5])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 215014751-(Cyanoamino)nonan-4-yl acetateHCID 22770549Ethyl 7-bromo-2-methylheptanoate

Product 1

HCID 86734144HCID 86734144, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A stirred suspension of sodium hydride (57% in mineral oil) (5.0 g., excess) in a solvent mixture of benzene (75 ml.) and dimethylformide (75 ml.) is treated, over 30 minutes, with 4-acetoxynonylcyanamide (22.6 g., 0.1 mole) (Example O, Step 5) dissolved in benzene (20 ml.). Stirring is continued for one hour. Then, ethyl 7-bromo-2-methylheptanoate (Example L, Step 4) (25.3 g., 0.1 mole) is added dropwise, and the reaction is heated on the steam bath for 3.5 hours. The cooled reaction is poured into water (400 ml.) and extracted with ethyl acetate (2 × 200 ml.). The organic fractions are combined, washed with brine, then dried over sodium sulfate. The solvent is removed in vacuo to give ethyl 7-[N-(4-acetoxynonyl)cyanamido]-2-methylheptanoate as a pale yellow liquid.

Workup

  1. temperaturethe reaction is heated on the steam bath for 3.5 hours
  2. customThe cooled reaction
  3. extractionextracted with ethyl acetate (2 × 200 ml.)
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-1741e1ff249d42b790b915bcb5f1312f
Source dataset
uspto-grants-1976_11
Patent number
US03989749

Reaction notes

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