Benzene, 1-isothiocyanato-4-nitro- → 2-(5-(2-hydroxypropan-2-yl)pyridin-2-yl)-N-(4-nitrophenyl)hydrazinecarbothioamide

HRID 1925130Notes

Reaction equation

HRID 1925130 reaction equation
[NH:1]([C:3]1[N:8]=[CH:7][C:6]([C:9]([OH:12])([CH3:11])[CH3:10])=[CH:5][CH:4]=1)[NH2:2].[N:13]([C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][CH:17]=1)=[C:14]=[S:15]>C(#N)C.CCOCC>[OH:12][C:9]([C:6]1[CH:5]=[CH:4][C:3]([NH:1][NH:2][C:14](=[S:15])[NH:13][C:16]2[CH:17]=[CH:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][CH:21]=2)=[N:8][CH:7]=1)([CH3:10])[CH3:11]

Participants

5

Reactant 2

HCID 75044Benzene, 1-isothiocyanato-4-nitro-HCID 552817922-(6-Hydrazinylpyridin-3-yl)propan-2-ol

Product 1

HCID 866398192-(5-(2-hydroxypropan-2-yl)pyridin-2-yl)-N-(4-nitrophenyl)hydrazinecarbothioamideYield 33.7%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(6-hydrazinylpyridin-3-yl)propan-2-ol (250 mg, 1.495 mmol) and 1-isothiocyanato-4-nitrobenzene (269 mg, 1.495 mmol) in ACN (Volume: 2.0 mL) was stirred at room temperature for 1 hr. The reaction was diluted with Et2O (Volume: 5.0 mL), and the resulting solid was filtered. Minimal product was present in the solid. On standing for 1 hr, the filtrate had formed a precipitate. This was filtered to provide 2-(5-(2-hydroxypropan-2-yl)pyridin-2-yl)-N-(4-nitrophenyl)hydrazinecarbothioamide (175 mg, 0.504 mmol, 33.7% yield) as an orange solid. A solution of 2-(5-(2-hydroxypropan-2-yl)pyridin-2-yl)-N-(4-nitrophenyl)hydrazinecarbothioamide (275 mg, 0.792 mmol) in DME (Volume: 2.0 mL) was heated in a microwave on high absorbance for 3 hr at 110° C. The reaction was stripped to dryness onto silica gel via rotary evaporation and purified compound by MPLC with DCM:MeOH (98:2) to provide 2-(3-mercapto-[1,2,4]triazolo[4,3-a]pyridin-6-yl)propan-2-ol.

Workup

  1. filtrationthe resulting solid was filtered
  2. waitOn standing for 1 hr
  3. customthe filtrate had formed a precipitate
  4. filtrationThis was filtered

Sources & evidence

ORD record
ord-97f8e5e85a3145a38c83f9b08864e8cf
Source dataset
uspto-grants-2012_05
Patent number
US08178534B2

Reaction notes

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