Hydrazine hydrate (1:1) → HCID 66737727, compound

HRID 1640968Notes

Reaction equation

HRID 1640968 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([S:9]([C:12]2[CH:13]=[CH:14][C:15]([N+:20]([O-])=O)=[C:16]([CH:19]=2)[C:17]#[N:18])(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1.O.[NH2:24]N>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([S:9]([C:12]2[CH:19]=[C:16]3[C:15](=[CH:14][CH:13]=2)[NH:20][N:18]=[C:17]3[NH2:24])(=[O:11])=[O:10])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 66736862HCID 66736862, compound

Product 1

HCID 66737727HCID 66737727, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-(3,5-Difluoro-benzenesulfonyl)-2-nitro-benzonitrile (3.5 g, 10.8 mmol) was heated in anhydrous ethanol (175 mL) until completely dissolved. The solution was then treated with hydrazine hydrate (0.58 mL, 1.1 mol eq.) and refluxed for three hours. The reaction mixture was evaporated to dryness; the residue was dissolved in acetone, adsorbed onto flash chromatography-grade silica gel by rotoevaporation of the solvent. The silica was loaded onto a flash chromatography column conditioned with 10:1 dichloromethane/acetone. The column was then eluted with dichloromethane/acetone (gradient: from 10:1 to 2:1) followed by a final washing with dichloromethane/acetone/methanol. The pure fractions were collected and evaporated to afford the title compound as a whitish crystalline powder (2.44 g, 73%).

Workup

  1. dissolutionuntil completely dissolved
  2. temperaturerefluxed for three hours
  3. customThe reaction mixture was evaporated to dryness
  4. dissolutionthe residue was dissolved in acetone
  5. washThe column was then eluted with dichloromethane/acetone (gradient: from 10:1 to 2:1)
  6. washa final washing with dichloromethane/acetone/methanol
  7. customThe pure fractions were collected
  8. customevaporated

Sources & evidence

ORD record
ord-57f4dee3bcf44f8c941ad9199a6cf6b6
Source dataset
uspto-grants-2012_02
Patent number
US08114865B2

Reaction notes

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