Isobutylamine → N,N'-Di-iso-butyl DL-malamide
Reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].[C:6]([O:16]CC)(=O)[CH:7]([CH2:9][C:10]([O:12]CC)=O)[OH:8]>>[CH2:1]([NH:5][C:6](=[O:16])[CH:7]([CH2:9][C:10]([NH:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[O:12])[OH:8])[CH:2]([CH3:4])[CH3:3]Participants
3
Procedure
N,N′-Di-iso-butyl DL-malamide was prepared by the reaction of iso-butylamine with diethyl DL-malate. To a round-bottomed flask were added diethyl DL-malate (5.229 g, 1 eq) and iso-butylamine (14.058 g, 7 eq). The clear light yellow solution was stirred for 24 hours at room temperature, after which point a white solid had precipitated from solution. The solid was filtered, washed with hexane (3×25 mL), and dried under vacuum (1.96 g, 29% yield). The product was >99% pure as determined by NMR analyses.
Workup
- customhad precipitated from solution
- filtrationThe solid was filtered
- washwashed with hexane (3×25 mL)
- customdried under vacuum (1.96 g, 29% yield)
Sources & evidence
- ORD record
- ord-06a0a58c9b2c427fa329d30afdb1183d
- Source dataset
- uspto-grants-2002_07
- Patent number
- US06413914B1
Reaction notes
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