Ammonia → HCID 21401682, compound

HRID 973345Notes

Reaction equation

HRID 973345 reaction equation
Cl[C:2]([CH:4]([CH2:16][CH2:17][CH2:18][CH:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:3].[NH3:29]>O.CCOCC>[C:2]([CH:4]([CH2:16][CH2:17][CH2:18][CH:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])(=[O:3])[NH2:29]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 20322197Ethyl 12-(acetyloxy)-8-(chlorocarbonyl)heptadecanoate

Product 1

HCID 21401682HCID 21401682, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

Ethyl 8-chlorocarbonyl-12-acetoxyheptadecanoate (8.38 g.; 0.02 mole) is added with stirring to a 28% solution of ammonia in water (concentrated ammonium hydroxide) (75 ml.). The amide forms at once and separates as a semi-solid. It is dissolved in ether, washed with water and dried over sodium sulfate. The ether is removed under vacuum to give the title compound as a semi-solid, yield 6.8 g. The product is purified by column chromatography on silica gel with 2% methanol in chloroform as eluant; pmr (CDCl3)δ 0.88 (3H,t), 2.02 (3H,s CH3COO), 4.12 (2H,q), 4.85 (1H,m HCO), 5.98 (2H,s NH2).

Workup

  1. washwashed with water
  2. dry with materialdried over sodium sulfate
  3. customThe ether is removed under vacuum

Sources & evidence

ORD record
ord-e5573b99044045e6bd5ad1db674905fc
Source dataset
uspto-grants-1977_10
Patent number
US04055597

Reaction notes

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