Hydrazine hydrate (1:1) → HCID 178438396, compound

HRID 2064592Notes

Reaction equation

HRID 2064592 reaction equation
[CH3:1][S:2][C:3](SC)=[C:4]([CH2:17][CH2:18][CH3:19])[C:5]([C:7]1[NH:11][C:10]2[CH:12]=[CH:13][C:14]([CH3:16])=[CH:15][C:9]=2[N:8]=1)=O.O.[NH2:23][NH2:24]>C(O)C>[CH3:16][C:14]1[CH:13]=[CH:12][C:10]2[NH:11][C:7]([C:5]3[C:4]([CH2:17][CH2:18][CH3:19])=[C:3]([S:2][CH3:1])[NH:24][N:23]=3)=[N:8][C:9]=2[CH:15]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178446990HCID 178446990, compound

Product 1

HCID 178438396HCID 178438396, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(bis-methylsulfanyl-methylene)-1-(5-methyl-1H-benzoimidazol-2-yl)-pentan-1-one [˜0.49 mmole, Reference Example 2(l)] and hydrazine hydrate (200 μL) in ethanol (6 mL) was heated at reflux temperature for 2 days, then evaporated. The mixture was then treated with hydrochloric acid (4 mL, 4N) and heating was continued at reflux temperature for a further 24 hours. The reaction mixture was cooled, then neutralised by addition of sodium hydroxide solution (4N) and then extracted with dichloromethane. The extract was evaporated to give 5-methyl-2-(5-methylsulfanyl-4-propyl-1H-pyrazol-3-yl)-1H-benzoimidazole. MS: 287 (M+H)+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 2 days
  3. customevaporated
  4. additionThe mixture was then treated with hydrochloric acid (4 mL, 4N)
  5. temperatureheating
  6. temperatureat reflux temperature for a further 24 hours
  7. temperatureThe reaction mixture was cooled
  8. additionneutralised by addition of sodium hydroxide solution (4N)
  9. extractionextracted with dichloromethane
  10. customThe extract was evaporated

Sources & evidence

ORD record
ord-a44c47b1c1ef48cb977b07de8f1c2ccf
Source dataset
uspto-grants-2012_10
Patent number
US08288425B2

Reaction notes

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