Ethylamine → N-Ethyl-2-isobutyl-2,4-dimethylvaleramide

HRID 848591Notes

Reaction equation

HRID 848591 reaction equation
[CH2:1]([C:5]([CH3:13])([CH2:9][CH:10]([CH3:12])[CH3:11])[C:6]([OH:8])=[O:7])[CH:2]([CH3:4])[CH3:3].[CH2:14]([C:16]#[N:17])C.C(Br)C(C)C.S(Cl)([Cl:25])=O.C(N)C>CCOCC.O>[CH2:1]([C:5]([CH3:13])([CH2:9][CH:10]([CH3:12])[CH3:11])[C:6]([Cl:25])=[O:7])[CH:2]([CH3:4])[CH3:3].[CH2:16]([NH:17][C:6](=[O:8])[C:5]([CH2:1][CH:2]([CH3:3])[CH3:4])([CH3:13])[CH2:9][CH:10]([CH3:12])[CH3:11])[CH3:14]

Participants

9

Reactant 5

HCID 6341EthylamineHCID 65551-Bromo-2-methylpropaneHCID 7854PropionitrileHCID 24386Thionyl ChlorideHCID 266760HCID 266760, compound

Product 2

HCID 3016606N-Ethyl-2-isobutyl-2,4-dimethylvaleramideHCID 20565978HCID 20565978, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

2-isobutyl-2,4-dimethylpentanoyl chloride (bp. 97°-100°/16 mm) was prepared in the usual way from 2-isobutyl-2,4-dimethylpentanoic acid (prepared by the alkylation of ethyl cyanide with 2 equivalents of isobutyl bromide, followed by hydrolysis) and thionyl chloride. A solution of the acid chloride (1.5 g) in ether (20 ml) was added with stirring to a solution of ethylamine (5 ml of a 70% solution in water) in ether (100 ml). After stirring for 2 hours the ethereal layer was washed with dilute hydrochloric acid and water. The dried (MgSO4) other solution was concentrated and the residue was recrystallised from petroleum ether (bp. 40°-60°) to give N-ethyl-2-isobutyl-2,4-dimethylpentanamide, mp. 71.5°-72.5°.

Workup

  1. washwas washed with dilute hydrochloric acid and water
  2. dry with materialThe dried (MgSO4) other solution
  3. concentrationwas concentrated
  4. customthe residue was recrystallised from petroleum ether (bp. 40°-60°)

Sources & evidence

ORD record
ord-358ed31041d84126ae66badeb2d50c70
Source dataset
uspto-grants-1981_10
Patent number
US04296255

Reaction notes

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