Isophorone diamine → 1-(1-Isobutoxycarbonyl-2-prop-1-enylamino)-3-(1-isobutoxycarbonyl-2-prop-1-enylaminomethyl)-3,5,5-trimethylcyclohexane

HRID 1060207

Reaction equation

HRID 1060207 reaction equation
[CH3:1][C:2]1([CH3:12])[CH2:7][C:6]([CH2:9][NH2:10])([CH3:8])[CH2:5][CH:4]([NH2:11])[CH2:3]1.[C:13]([O:19][CH2:20][CH:21]([CH3:23])[CH3:22])(=[O:18])[CH2:14][C:15]([CH3:17])=O>CO>[CH2:20]([O:19][C:13]([CH:14]=[C:15]([NH:11][CH:4]1[CH2:3][C:2]([CH3:12])([CH3:1])[CH2:7][C:6]([CH:9]([NH:10][C:15]([CH3:17])=[CH2:14])[C:13]([O:19][CH2:20][CH:21]([CH3:23])[CH3:22])=[O:18])([CH3:8])[CH2:5]1)[CH3:17])=[O:18])[CH:21]([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 17857Isophorone diamineHCID 522677Isobutyl acetoacetate

Product 1

HCID 698581921-(1-Isobutoxycarbonyl-2-prop-1-enylamino)-3-(1-isobutoxycarbonyl-2-prop-1-enylaminomethyl)-3,5,5-trimethylcyclohexaneYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To isophoronediamine (139.23 g, 0.819 mol) in methanol (700 ml) was slowly added with stirring isobutyl acetoacetate (262.31 g, 1.660 mol) in methanol (700 ml) over 45 minutes, during which the temperature increased from 22° C. to 30° C. The reaction mixture was allowed to stand at 21° C. overnight (15 h). Further methanol was added, and removal of solvent and drying (91° C./100 Pa) gave 1-(1-isobutoxycarbonyl-2-prop-1-enylamino)-3-(1-isobutoxycarbonyl-2-prop-1-enylaminomethyl)-3,5,5-trimethylcyclohexane (IIMTCH) as a clear light yellow viscous syrup (366.80 g, 100%), which set to a soft gum on standing and was identified by 1H-NMR, 13C-NMR, FT-IR and Raman spectra.

Workup

  1. temperatureincreased from 22° C. to 30° C
  2. custom(15 h)
  3. customremoval of solvent
  4. customdrying (91° C./100 Pa)

Sources & evidence

ORD record
ord-01d6ba5754764b41bbc2f4b9915834c2
Source dataset
uspto-grants-2003_02
Patent number
US06521716B1

Linked notes

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