Isopropanol → HCID 21441211, compound

HRID 328293Notes

Reaction equation

HRID 328293 reaction equation
[CH3:1][NH:2][NH2:3].C(O)(C)C.[CH:8]1([C:14](=O)[CH:15]([CH3:24])[C:16]([CH:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]2)=O)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>O>[CH:8]1([C:14]2[C:15]([CH3:24])=[C:16]([CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[N:2]([CH3:1])[N:3]=2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 6061Methylhydrazine3×HCID 21441225HCID 21441225, compound

Product 1

HCID 21441211HCID 21441211, compoundYield 32.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

Methylhydrazine (1.0 g, 0.022 mole) is added at 60° C-70° C with stirring to an isopropanol (200 ml) solution of 1,3-dicyclohexyl-2-methyl-1,3-propanedione (5.0 g, 0.02 mole) having a m.p. =36°--37° C and prepared by the procedure of Example 3 above. The reaction is heated at reflux for 4 hours, then cooled, water (300 ml) added and the resulting solid filtered off. The solid is dissolved in anhydrous toluene, methyl hydrazine (1.0 g, 0.022 mole) added and the reaction mixture heated at 90° C for 4 hours. Then additional methyl hydrazine (1.0 g, 0.022 mole) is added and heating continued for 3 hours. The reaction mixture is cooled. The solvent removed on a rotary evaporator and the resulting solid crystallized from hexane/benzene to give 1.7 g (32%) of the desired product, m.p. 120° C to 122° C.

Workup

  1. customa m.p. =36°--37° C
  2. customprepared by the procedure of Example 3 above
  3. temperatureThe reaction is heated
  4. temperatureat reflux for 4 hours
  5. temperaturecooled
  6. filtrationthe resulting solid filtered off
  7. dissolutionThe solid is dissolved in anhydrous toluene
  8. temperatureheating
  9. temperatureThe reaction mixture is cooled
  10. customThe solvent removed on a rotary evaporator
  11. customthe resulting solid crystallized from hexane/benzene

Sources & evidence

ORD record
ord-b7510e1e37d540d5a81252c552e3e9cf
Source dataset
uspto-grants-1977_04
Patent number
US04017298

Reaction notes

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