Acetic Acid → 1,1-Dimethylethyl 2-[(4-bromo-2-fluorophenyl)(tetrahydro-3-furanyl)methylidene]hydrazinecarboxylate

HRID 2246615Notes

Reaction equation

HRID 2246615 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:14][CH2:13][O:12][CH2:11]2)=O)=[C:4]([F:15])[CH:3]=1.[NH:16]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[NH2:17].C(O)(=O)C>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]2[CH2:14][CH2:13][O:12][CH2:11]2)=[N:17][NH:16][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[C:4]([F:15])[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 70091tert-Butyl carbazateHCID 58899605(4-Bromo-2-fluorophenyl)(tetrahydro-3-furanyl)methanone2×

Product 1

HCID 724574151,1-Dimethylethyl 2-[(4-bromo-2-fluorophenyl)(tetrahydro-3-furanyl)methylidene]hydrazinecarboxylateYield 91.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of ((4-bromo-2-fluorophenyl)(tetrahydro-3-furanyl)methanone (Intermediate 7, 850 mg) 1,1-dimethylethyl hydrazinecarboxylate (616 mg) and acetic acid (1 mL) in methanol (5 mL) was stirred at reflux under nitrogen for 20 h. The solvent was removed under vacuum and the residue was partitioned between ethyl acetate and water. The organic phase was washed with sodium bicarbonate (1M, 10 mL), dried using a hydrophobic filter tube and concentrated under vacuum to give the title compound as a brown oil (1.1 g).

Workup

  1. temperatureat reflux under nitrogen for 20 h
  2. customThe solvent was removed under vacuum
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic phase was washed with sodium bicarbonate (1M, 10 mL)
  5. customdried
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-da954334a88e4b0dab79fc4a338c2c1d
Source dataset
uspto-grants-2010_03
Patent number
US07687532B2

Reaction notes

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