Hydrazine → HCID 178514377, compound

HRID 897882Notes

Reaction equation

HRID 897882 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=S)=[CH:4][CH:3]=1.[NH2:18][NH2:19]>C(O)C.O1CCCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[F:17])=[N:18][NH2:19])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 9321Hydrazine2×HCID 22346994HCID 22346994, compound

Product 1

HCID 178514377HCID 178514377, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

N1-(4-bromophenyl)-2-fluoro-1-benzenecarbothioamide (1.50 g, 0.00485 mol) and a 1M solution of hydrazine in tetrahydrofuran (6.3 mL, 0.0063 mol) were heated in absolute ethanol (25 mL) at reflux under nitrogen atmosphere for 14 hours. Additional 3 mL of a 1M solution of hydrazine in tetrahydrofuran was added and the stirring at reflux was continued for another 6 hours. The reaction mixture was cooled to ambient temperature, the solvent was removed under reduced pressure and the residue partitioned between saturated solution of sodium bicarbonate in water (50 mL) and ethyl acetate (50 mL). The organic phase was washed with brine, dried with magnesium sulfate and concentrated to yield N1-(4-bromophenyl)-2-fluoro-1-benzenecarbohydrazonamide (1.54 g, 0.0050 mol) as a tan solid. TLC (ethyl acetate/heptane 1:3) Rf 0.10.

Workup

  1. temperatureat reflux under nitrogen atmosphere for 14 hours
  2. temperaturethe stirring at reflux
  3. customthe solvent was removed under reduced pressure
  4. customthe residue partitioned between saturated solution of sodium bicarbonate in water (50 mL) and ethyl acetate (50 mL)
  5. washThe organic phase was washed with brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cbd6a40a301c4f92908b9733dcf0ba7c
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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