Isoniazid → 2-isonicotinoyl-N-methylhydrazinecarbothioamide

HRID 1453803Notes

Reaction equation

HRID 1453803 reaction equation
[C:1]([NH:9][NH2:10])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[CH3:11][N:12]=[C:13]=[S:14]>C(O)(C)C>[C:1]([NH:9][NH:10][C:13](=[S:14])[NH:12][CH3:11])(=[O:8])[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3767IsoniazidHCID 11167Methyl isothiocyanate

Product 1

HCID 28240222-isonicotinoyl-N-methylhydrazinecarbothioamideYield 93%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Conditions

Temperature
70 °C

Procedure

To a gently heated (35° C.) and mechanically stirred suspension of isonicotinohydrazide (435 g) in isopropyl alcohol (6.0 L) was added (methylimino)(thioxo)methane (230 g) in several small portions. After complete addition, the reaction mixture was heated (70° C.) for 6 h with an additional addition of isopropyl alcohol (600 ml) after 30 min. After cooling (ice-bath) the reaction mixture to 17° C., the obtained precipitate was filtered off and washed with isopropyl alcohol (1.0 L). This solid was then air-dried over night to provide 615 g of the title compound as a white powder.

Workup

  1. temperatureTo a gently heated
  2. additionAfter complete addition
  3. temperatureAfter cooling (ice-bath) the reaction mixture to 17° C.
  4. filtrationthe obtained precipitate was filtered off
  5. washwashed with isopropyl alcohol (1.0 L)
  6. customThis solid was then air-dried over night

Sources & evidence

ORD record
ord-033d4fd64219454ba9c91fef246073ee
Source dataset
uspto-grants-2009_01
Patent number
US07476684B2

Reaction notes

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