N-Methylhydrazinecarbothioamide → 2-[4-Chloro-1-(pyridin-3-yl)-butylidene]-N-methyl-hydrazinecarbothioamide

HRID 613681Notes

Reaction equation

HRID 613681 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)=O.[CH3:13][NH:14][C:15](=[S:18])[NH:16][NH2:17]>C(O)C>[Cl:1][CH2:2][CH2:3][CH2:4][C:5](=[N:17][NH:16][C:15](=[S:18])[NH:14][CH3:13])[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 2723853N-MethylhydrazinecarbothioamideHCID 124710054-Chloro-1-(pyridin-3-YL)butan-1-one

Product 1

HCID 544744142-[4-Chloro-1-(pyridin-3-yl)-butylidene]-N-methyl-hydrazinecarbothioamideYield 112.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-chloro-1-(3-pyridinyl)-1-butanone (4.4 g, 24 mmol) and 4-methylthiosemicarbazide (2.5 g, 24 mmol) in 150 mL of ethanol under a nitrogen atmosphere was warmed to dissolve all the solids and then allowed to stir at room temperature overnight. By TLC the reaction was not complete. The reaction was then heated at 70° C. for 5 hours and overnight at room temperature. The solvent was removed under reduced pressure to give 7.29 g of a yellow oil. Purification of this oil on 700 g of silica gel (230-400 mesh) using 50-70% EtOAc-hexane as the eluent gave 4.14 g (64%) of the title compound as a white solid, mp 100-102° C.

Workup

  1. temperaturewas warmed
  2. dissolutionto dissolve all the solids
  3. temperatureThe reaction was then heated at 70° C. for 5 hours and overnight at room temperature
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0b3210bde09d4528a1999574f3a04593
Source dataset
uspto-grants-1999_12
Patent number
US06008362

Reaction notes

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