Water → HCID 20497722, compound

HRID 2166805Notes

Reaction equation

HRID 2166805 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[NH2:12])[CH:5]=[CH:4][CH:3]=1.CC([CH2:16][C:17](=O)[CH:18]([CH3:24])[CH2:19][CH:20]([CH3:23])[CH2:21]C)C.O.C([O-])([O-])=O.[K+].[K+].[CH2:33](O)[CH:34]([CH3:36])[CH3:35]>CCCCCC.C(OCC)C.C(O)(=O)C>[CH2:33]([C:16]1([CH2:17][CH:18]([CH3:24])[CH2:19][CH:20]([CH3:23])[CH3:21])[NH:12][C:10]2[C:11]3[C:6]([CH:7]=[CH:8][CH:9]=2)=[CH:5][CH:4]=[CH:3][C:2]=3[NH:1]1)[CH:34]([CH3:36])[CH3:35]

Participants

8

Reactant 5

HCID 962WaterHCID 6560IsobutanolHCID 11430Potassium CarbonateHCID 680671,8-DiaminonaphthaleneHCID 20497717HCID 20497717, compound

Product 1

HCID 20497722HCID 20497722, compoundYield 36.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 21584099Diethylether hexaneSolvent

Procedure

15.8 g (0.1 mole) of 1,8-diaminonaphthalene and 16.0 g (0.1 mole) of 2,5,7-trimethyl-4-nonanone were dissolved in a mixture of 52 g of isobutanol, 24 g of water and 9 g of acetic acid and heated under reflux for 11 hours. After cooling, the solution was neutralized with 3.0 g of K2CO3. The organic layer was separated from the aqueous layer and filtered. The filtrate was evaporated in vacuo yielding a dark oily residue, which was thereafter dissolved in 2:1 hexane-diethylether and the solution filtered over alumina. After distilling off the solvent, 11.8 g of 2-isobutyl-2(2,4-dimethylpentyl)-2,3-dihydroperimidine was obtained as a semi-solid residue (Compound No. 17)

Workup

  1. temperatureheated
  2. temperatureunder reflux for 11 hours
  3. temperatureAfter cooling
  4. customThe organic layer was separated from the aqueous layer
  5. filtrationfiltered
  6. customThe filtrate was evaporated in vacuo
  7. customyielding a dark oily residue, which
  8. filtrationthe solution filtered over alumina
  9. distillationAfter distilling off the solvent

Sources & evidence

ORD record
ord-c6ef38b732774234b5e5f71eda72eb41
Source dataset
uspto-grants-1983_06
Patent number
US04389321

Reaction notes

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