Hydrazine hydrate (1:1) → 2-(5-Amino-3-methyl-1H-pyrazol-4-yl)benzothiazole-5-sulfonic acid methylamide

HRID 407300Notes

Reaction equation

HRID 407300 reaction equation
[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([C:14]([C:19]#[N:20])=[C:15](OC)[CH3:16])=[N:11][C:10]=2[CH:21]=1)(=O)=[O:4].[OH2:22].[NH2:23][NH2:24]>CO.Cl>[CH3:1][NH:2][S:3]([C:6]1[CH:7]=[CH:8][C:9]2[S:13][C:12]([C:14]3[C:15]([CH3:16])=[N:23][NH:24][C:19]=3[NH2:20])=[N:11][C:10]=2[CH:21]=1)(=[O:4])=[O:22]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 667682252-(1-Cyano-2-methoxypropenyl)benzothiazole-5-sulfonic acid methylamide

Product 1

HCID 1784862662-(5-Amino-3-methyl-1H-pyrazol-4-yl)benzothiazole-5-sulfonic acid methylamideYield 43%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 2-(1-cyano-2-methoxypropenyl)benzothiazole-5-sulfonic acid methylamide (120 mg, 0.37 mmol) in 4 mL of methanol, was added hydrazine hydrate (20 μL). The mixture was heated to reflux for 5 hrs and then 1 drop of conc. hydrochloric acid was added to the reaction mixture. The mixture was refluxed for an additional 5 min and was then allowed to cool. The volume of solvent was reduced under reduced pressure and a solid formed. The solid was isolated by filtration and was washed with methanol and then water and dried to yield 51 mg (43%) of the title compound as a cream coloured powder. MS (m/z, ES+): 324.0 (M+1, 100%).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 hrs
  3. temperatureThe mixture was refluxed for an additional 5 min
  4. temperatureto cool
  5. customa solid formed
  6. customThe solid was isolated by filtration
  7. washwas washed with methanol
  8. dry with materialwater and dried

Sources & evidence

ORD record
ord-f7f6a72e11524d9a9d1160e75679c0c3
Source dataset
uspto-grants-2014_06
Patent number
US08754233B2

Reaction notes

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