Cyclopropanecarbohydrazide → HCID 68500854, compound

HRID 888378Notes

Reaction equation

HRID 888378 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[CH:6]=[C:7]([CH:15]=[C:16]([C:18]2[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=2)[CH:17]=1)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=S.[CH:25]1([C:28]([NH:30][NH2:31])=O)[CH2:27][CH2:26]1>O1CCCC1.C([O-])(=O)C.[Hg+2].C([O-])(=O)C>[CH:25]1([C:28]2[N:2]([CH3:1])[C:3]([C:5]3[CH:6]=[C:7]([CH:15]=[C:16]([C:18]4[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][N:19]=4)[CH:17]=3)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[N:31][N:30]=2)[CH2:27][CH2:26]1

Participants

5

Reactant 2

HCID 81396CyclopropanecarbohydrazideHCID 86646757HCID 86646757, compound

Product 1

HCID 68500854HCID 68500854, compound

Reagents, catalysts & solvents 2

HCID 15337Mercuric acetateCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of tert-butyl 3-[(methylamino)carbonothioyl]-5-(5-methylpyridin-2-yl)benzoate (0.56 g, 1.64 mmol) in tetrahydrofuran (15 mL) were added cyclopropanecarbohydrazide (0.49 g, 4.92 mmol) and mercury(II) acetate (1.05 g, 3.28 mmol). The reaction mixture was heated to 40° C. After 18 h, the mixture was cooled to ambient temperature. The mixture was filtered and the filtrate was concentrated. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) gave the title compound. MS 391.1 (M+1).

Workup

  1. temperaturethe mixture was cooled to ambient temperature
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customPurification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol)

Sources & evidence

ORD record
ord-002b095d04b54a978a6f6985bd50d702
Source dataset
uspto-grants-2012_08
Patent number
US08247401B2

Reaction notes

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