Hydrazine, dihydrochloride → HCID 18954842, compound

HRID 2380664Notes

Reaction equation

HRID 2380664 reaction equation
Cl.Cl.[NH2:3][NH2:4].[CH:5]([C:7]1[CH:20]=[CH:19][CH:18]=[CH:17][C:8]=1[O:9][CH2:10][C:11](=[CH2:16])[C:12]([O:14][CH3:15])=[O:13])=O.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:28]=[CH:27][C:26]([N:29]=[C:30]=[O:31])=[CH:25][CH:24]=1>C(O)(C)(C)C.O>[F:21][C:22]([F:32])([F:33])[C:23]1[CH:24]=[CH:25][C:26]([NH:29][C:30]([N:3]2[CH2:16][C:11]3([C:12]([O:14][CH3:15])=[O:13])[CH2:10][O:9][C:8]4[CH:17]=[CH:18][CH:19]=[CH:20][C:7]=4[CH:5]3[NH:4]2)=[O:31])=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 17548Hydrazine, dihydrochlorideHCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 18954848HCID 18954848, compound

Product 1

HCID 18954842HCID 18954842, compoundYield 7.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6386tert-ButanolSolvent

Procedure

A solution of 7.15 g (0.0681 mol) of hydrazine dihydrochloride in 95 mL of tert-butanol and 5 mL of water was heated at reflux for 1/2 hour at which time 1.50 g (0.0068 mol) of the product from Step A was added all at once. The reaction mixture was refluxed for 20 hours and the solvent was removed by evaporation under reduced pressure. 200 mL of 1N sodium hydroxide was added and the crude product was extracted with ethyl acetate (3×75 mL). The ethyl acetate was washed with water (100 mL), dried over anhydrous magnesium sulfate, filtered into a flask containing 1.27 g (0.0068 mol) of α,α,α-trifluoro-p-tolylisocyanate. The reaction mixture was stirred at room temperature for 1/2 hour, the solvent was removed under reduced pressure and the crude product was chromatographed using ether/hexanes (35%:65%) as eluent to afford 0.219 g of a white solid; mp 211°-212° C.

Workup

  1. additionwas added all at once
  2. temperatureThe reaction mixture was refluxed for 20 hours
  3. customthe solvent was removed by evaporation under reduced pressure
  4. addition200 mL of 1N sodium hydroxide was added
  5. extractionthe crude product was extracted with ethyl acetate (3×75 mL)
  6. washThe ethyl acetate was washed with water (100 mL)
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered into a flask
  9. customthe solvent was removed under reduced pressure
  10. customthe crude product was chromatographed

Sources & evidence

ORD record
ord-a60a2a4881764e5d8ef76462f316c2b0
Source dataset
uspto-grants-1994_11
Patent number
US05369121

Reaction notes

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