Methylhydrazine → N-Methyl Octadecenyl Succinhydrazide

HRID 48918Notes

Reaction equation

HRID 48918 reaction equation
[CH:1]([CH:19]1[CH2:24][C:23](=[O:25])O[C:20]1=[O:21])=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].[CH3:26][NH:27][NH2:28].[NH2:29][NH2:30]>O.C1(C)C=CC=CC=1>[CH3:26][N:27]([C:20](=[O:21])[CH:19]([CH:1]=[CH:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:24][C:23]([NH:29][NH2:30])=[O:25])[NH2:28]

Participants

6

Reactant 3

HCID 6061MethylhydrazineHCID 9321HydrazineHCID 225771Dihydro-3-(1-octadecen-1-yl)-2,5-furandione

Product 1

HCID 86588301N-Methyl Octadecenyl Succinhydrazide

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 1140TolueneSolvent2×

Procedure

Into a 250 mL three-necked round-bottomed flask, equipped with a mechanical stirrer, Dean-Stark water trap, addition funnel, thermocouple to temperature controller, heating mantle, and a nitrogen blanket is charged 75 mL of toluene and 17.1 grams (0.05 mole) of octadecenyl succinic anhydride. In the addition funnel is charged 2.3 grams (0.05 mole) of methylhydrazine. The hydrazine is slowly added dropwise to the stirred reaction media at room temperature over a five minute period. The reaction media showed little exotherm. The temperature is then raised to reflux the toluene to the Dean-Stark trap. The reaction media are refluxed until water is no longer removed and the infrared analysis of a sampled product shows all the anhydride has been converted to succinhydrazide. The reaction media are now cooled to room temperature and placed on a Roto-Evaporator to remove the toluene solvent. The reaction product is now filtered through a bed of Celite filter-aid to yield 18.4 grams of a clear yellow liquid.

Workup

  1. customInto a 250 mL three-necked round-bottomed flask, equipped with a mechanical stirrer
  2. temperaturethermocouple to temperature controller, heating mantle
  3. customThe reaction media
  4. temperatureThe temperature is then raised
  5. customThe reaction media
  6. customno longer removed
  7. customThe reaction media
  8. customplaced on a Roto-Evaporator
  9. customto remove the toluene solvent
  10. filtrationThe reaction product is now filtered through a bed of Celite
  11. filtrationfilter-aid

Sources & evidence

ORD record
ord-6e210c49fae345b0933309942827761f
Source dataset
uspto-grants-2004_03
Patent number
US06706671B2

Reaction notes

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