Isophorone diamine → HCID 69858841, compound

HRID 1060208Notes

Reaction equation

HRID 1060208 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.[CH3:13][CH2:14][CH2:15][C:16]([CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=O>CO>[CH2:22]([O:21][C:19]([CH:18]=[C:16]([NH:11][CH:4]1[CH2:3][C:2]([CH3:12])([CH3:1])[CH2:7][C:6]([CH:9]([NH:10][C:14]([CH2:15][CH2:16][CH3:18])=[CH2:13])[C:19]([O:21][CH2:22][CH3:23])=[O:20])([CH3:8])[CH2:5]1)[CH2:15][CH2:14][CH3:13])=[O:20])[CH3:23]

Participants

4

Reactant 2

HCID 17857Isophorone diamineHCID 238498Ethyl 3-oxohexanoate

Product 1

HCID 69858841HCID 69858841, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

To isophoronediamine (139.23 g, 0.819 mol) in methanol (700 ml) was slowly added with stirring ethyl butyroacetate (262.32 g, 1.660 mol) in methanol (700 ml) over 45 minutes, during which the temperature decreased slightly from 24° C. to 23° C. The reaction mixture was allowed to stand at 22° C. overnight (16 h). Further methanol was added, and removal of solvent and drying (91° C./100 Pa) gave 1-(1-ethoxycarbonyl-2-pent-1-enylamino)-3-(1-ethoxycarbonyl-2-pent-1-enylaminomethyl)-3,5,5-trimethylcyclohexane (EEMTCH formula shown below) as a clear light yellow pourable syrup (356.74 g, 97%), identified by 1H-NMR, 13C-NMR, FT-IR and Raman spectra.

Workup

  1. customdecreased slightly from 24° C. to 23° C
  2. custom(16 h)
  3. customremoval of solvent
  4. customdrying (91° C./100 Pa)

Sources & evidence

ORD record
ord-f096900657d94d8ebe0265e3273590e2
Source dataset
uspto-grants-2003_02
Patent number
US06521716B1

Reaction notes

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