Thiosemicarbazide → 5-(2,2,3,3-Tetrafluoro-1-methylcyclobutyl)-1,3,4-thiadiazol-2-amine

HRID 717225Notes

Reaction equation

HRID 717225 reaction equation
[F:1][C:2]1([F:12])[C:5]([F:7])([F:6])[CH2:4][C:3]1([CH3:11])[C:8](Cl)=O.[NH2:13][NH:14][C:15]([NH2:17])=[S:16]>O1CCOCC1>[F:1][C:2]1([F:12])[C:5]([F:7])([F:6])[CH2:4][C:3]1([C:8]1[S:16][C:15]([NH2:17])=[N:14][N:13]=1)[CH3:11]

Participants

4

Reactant 2

HCID 2723789ThiosemicarbazideHCID 533989902,2,3,3-Tetrafluoro-1-(methyl)cyclobutanecarbonyl chloride

Product 1

HCID 866298495-(2,2,3,3-Tetrafluoro-1-methylcyclobutyl)-1,3,4-thiadiazol-2-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,2,3,3-tetrafluoro-1-methylcyclobutanecarbonyl chloride (ABCR) (2 g, 9.78 mmol) and thiosemicarbazide (Aldrich) (0.891 g, 9.78 mmol) in 10 mL of dioxane was heated at 90° C. for 12 h. The solvent was evaporated under reduced pressure. The residue was dissolved in dichloromethane and washed with saturated NaHCO3. The organic extract was dried over Na2SO4 and concentrated. The residue was purified by flash chromatography on SiO2 (2% methanol in dichloromethane) to give the title compound. MS (ESI+) m/z 242 (M+H)+.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane
  3. washwashed with saturated NaHCO3
  4. extractionThe organic extract
  5. dry with materialwas dried over Na2SO4
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography on SiO2 (2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-cec3a18d108d4608890470a4b1e454e7
Source dataset
uspto-grants-2015_11
Patent number
US09193713B2

Reaction notes

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