Isopropylamine → N-isopropyl-2,3-dimethyl-2-(1-methylpropyl)valeramide

HRID 904105Notes

Reaction equation

HRID 904105 reaction equation
[CH:1]([C:5]([CH3:13])([CH:9]([CH3:12])[CH2:10][CH3:11])[C:6]([OH:8])=[O:7])([CH2:3][CH3:4])[CH3:2].S(Cl)([Cl:16])=O.[CH:18]([NH2:21])([CH3:20])[CH3:19]>CCOCC>[CH:1]([C:5]([CH3:13])([CH:9]([CH3:12])[CH2:10][CH3:11])[C:6]([Cl:16])=[O:7])([CH2:3][CH3:4])[CH3:2].[CH:18]([NH:21][C:6](=[O:8])[C:5]([CH:1]([CH2:3][CH3:4])[CH3:2])([CH3:13])[CH:9]([CH3:12])[CH2:10][CH3:11])([CH3:20])[CH3:19]

Participants

6

Reactant 3

HCID 6363IsopropylamineHCID 24386Thionyl ChlorideHCID 20565973HCID 20565973, compound

Product 2

HCID 3016608N-isopropyl-2,3-dimethyl-2-(1-methylpropyl)valeramideHCID 20565976HCID 20565976, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

2-sec-butyl-2,3-dimethylpentanoyl chloride (bp. 108°-110°/17 mm) was prepared in the usual way from 2-sec-butyl-2,3-dimethylpentanoic acid and thionyl chloride. A solution of this acid chloride (2.0 g) in ether (30 ml) was added with stirring to a solution of isopropylamine (2.0 g) in ether (100 ml). After 16 hours the ethereal solution was washed with dilute hydrochloric acid and water, dried (MgSO4), and concentrated to give a white solid. This solid was recrystallized from petroleum ether (bp. 40°-60°) to give N-isopropyl-2-sec-butyl-2,3-dimethylpentanamide, MP. 74°-6°.

Workup

  1. washAfter 16 hours the ethereal solution was washed with dilute hydrochloric acid and water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customto give a white solid
  5. customThis solid was recrystallized from petroleum ether (bp. 40°-60°)

Sources & evidence

ORD record
ord-70364f7e317d4199a068616c058ca5d9
Source dataset
uspto-grants-1980_10
Patent number
US04230688

Reaction notes

Loading…