Hydrazinecarboxaldehyde → 4-(3',5'-Difluorobenzyl)-1-formyl-3-thiosemicarbazide

HRID 1248937Notes

Reaction equation

HRID 1248937 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([F:12])[CH:11]=1)[CH2:5][N:6]=[C:7]=[S:8].[CH:13]([NH:15][NH2:16])=[O:14]>C(O)C>[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([F:12])[CH:11]=1)[CH2:5][NH:6][C:7](=[S:8])[NH:16][NH:15][CH:13]=[O:14]

Participants

4

Reactant 2

HCID 12229HydrazinecarboxaldehydeHCID 201291633,5-Difluorobenzyl isothiocyanate

Product 1

HCID 202257224-(3',5'-Difluorobenzyl)-1-formyl-3-thiosemicarbazideYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,5-Difluorobenzyl isothiocyanate (9.9 g, 25.5 mmole) and formyl hydrazine (1.7 g, 28.7 mole) were refluxed in ethanol (30 ml) for one hour. The reaction was evaporated to dryness, triturated with hexane:ethyl acetate (1:1), filtered, and recrystallized from ethanol-hexane to yield 3.5 g (35%) of crude 4-(3',5'-difluorobenzyl)-1-formyl-3-thiosemicarbazide.

Workup

  1. customThe reaction was evaporated to dryness
  2. customtriturated with hexane:ethyl acetate (1:1)
  3. filtrationfiltered
  4. customrecrystallized from ethanol-hexane

Sources & evidence

ORD record
ord-4dc888b8db6742b1b616bfaa639e4d60
Source dataset
uspto-grants-1986_12
Patent number
US04628059

Reaction notes

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