Hydrazine → 2-[Hydrazonomethyl]phenyl 4-(trifluoromethyl)benzenesulfonate

HRID 1795103Notes

Reaction equation

HRID 1795103 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]=O)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[NH2:23][NH2:24]>C(O)C>[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([S:9]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH:19]=[N:23][NH2:24])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 221856712-Formylphenyl 4-(trifluoromethyl)benzenesulfonate

Product 1

HCID 738686872-[Hydrazonomethyl]phenyl 4-(trifluoromethyl)benzenesulfonateYield 89%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2-formylphenyl 4-(trifluoromethyl)benzenesulfonate (1.7 g, 5.1 mmol) in warm ethanol (100 mL) is added dropwise over 1 hour into a solution of hydrazine (6 equiv) in ethanol (5 mL). The reaction is stirred at room temperature overnight at which time the solvent is evaporated to dryness. The crude product is recrystallized from CH2Cl2/hexane to remove a dimer by-product. An 89% yield of 2-[hydrazonomethyl]phenyl 4-(trifluoromethyl)benzenesulfonate (4.65 g) is obtained.

Workup

  1. customis evaporated to dryness
  2. customThe crude product is recrystallized from CH2Cl2/hexane
  3. customto remove a dimer by-product

Sources & evidence

ORD record
ord-da48242e0f7b4d7e9a14fafad4ae63c6
Source dataset
uspto-grants-2006_04
Patent number
US07026339B2

Reaction notes

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