Isobutylamine → HCID 22457194, compound

HRID 381196Notes

Reaction equation

HRID 381196 reaction equation
[CH2:1]([NH2:5])[CH:2]([CH3:4])[CH3:3].C([CH:8]([C:22]([O-:24])=O)[C:9]([C:19]([O-:21])=O)([OH:18])[C:10](CC)(CC)[C:11]([O-:13])=O)C>CO>[CH2:1]([NH:5][C:11](=[O:13])[CH2:10][C:9]([CH2:8][C:22]([NH:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[O:24])([C:19]([NH:5][CH2:1][CH:2]([CH3:4])[CH3:3])=[O:21])[OH:18])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 6558Isobutylamine3×HCID 21193475HCID 21193475, compound2×

Product 1

HCID 22457194HCID 22457194, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N,N′,N″-tri-iso-butylcitramide was prepared by the reaction of iso-butylamine with triethylcitrate. To a round-bottomed flask were added triethylcitrate (30.001 g; 1 eq), iso-butylamine (24.034 g; 3.03 eq) and methanol (40 mL). The clear light yellow solution stirred for 2 days at room temperature and then additional isobutylamine (3.06 eq) was added. After stirring overnight, a wet white solid was observed. Methanol was removed in vacuo and the solid was triturated using diethylether, collected via filtration and dried in vacuo to give a white powder with no detectable odor (31.09 g; 80.3% yield).

Workup

  1. stirringAfter stirring overnight
  2. customMethanol was removed in vacuo
  3. customthe solid was triturated
  4. filtrationcollected via filtration
  5. customdried in vacuo
  6. customto give a white powder with no detectable odor (31.09 g; 80.3% yield)

Sources & evidence

ORD record
ord-145d0acc2e7a435da73173bf43be3161
Source dataset
uspto-grants-2001_10
Patent number
US06306463B1

Reaction notes

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