1,1-Dimethylhydrazine → HCID 54457896, compound

HRID 1606612Notes

Reaction equation

HRID 1606612 reaction equation
C(NC(=O)/C=C(\O[C:11](=[O:30])[C:12]1[CH:17]=[C:16]([S:18]([CH3:21])(=[O:20])=[O:19])[C:15]([Cl:22])=[CH:14][C:13]=1[NH:23][CH2:24][C:25]1[O:29][CH:28]=[CH:27][CH:26]=1)/C)(C)(C)C.[CH3:32][N:33]([NH2:35])[CH3:34]>C(#N)C>[CH3:32][N:33]([CH3:34])[NH:35][C:11](=[O:30])[C:12]1[CH:17]=[C:16]([S:18]([CH3:21])(=[O:19])=[O:20])[C:15]([Cl:22])=[CH:14][C:13]=1[NH:23][CH2:24][C:25]1[O:29][CH:28]=[CH:27][CH:26]=1

Participants

4

Reactant 2

HCID 59761,1-Dimethylhydrazine2×HCID 21543983HCID 21543983, compound

Product 1

HCID 54457896HCID 54457896, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

N-tert-butyl-3-(2-furfurylamino-4-chloro-5-methylsulfonylbenzoyloxy)crotonamide (4.69 g.; 0.01 mole) and unsymmetrical-dimethylhydrazine (1.20 g.; 0.02 mole) are added to acetonitrile. The reaction mixture is refluxed with stirring for 24 hours. Additional unsymmetrical-dimethylhyrazine (1.20 g.; 0.02 mole) is added, and refluxing is continued for an additional 24 hours. The acetonitrile is removed under reduced pressure, and the dark residue is triturated with isopropyl alcohol. The tan colored solid which crystallizes is collected and dried, yield 2.4 g. (64%), m.p. 90° -104° C. Several recrystallizations from butyl chloride followed by a recrystallization from benzene yields 2-furfurylamino-4-chloro-5-methylsulfonylbenzoic acid 2,2-dimethylhydrazide in the form of a white solid, m.p. 169.5°-171° C.

Workup

  1. temperatureThe reaction mixture is refluxed
  2. temperaturerefluxing
  3. waitis continued for an additional 24 hours
  4. customThe acetonitrile is removed under reduced pressure
  5. customthe dark residue is triturated with isopropyl alcohol
  6. customThe tan colored solid which crystallizes
  7. customis collected
  8. customdried
  9. customSeveral recrystallizations from butyl chloride
  10. customfollowed by a recrystallization from benzene

Sources & evidence

ORD record
ord-352a8286933c4b22af8a156a49919e66
Source dataset
uspto-grants-1976_04
Patent number
US03953476

Reaction notes

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