Hydrazine hydrate (1:1) → HCID 178509111, compound

HRID 407331Notes

Reaction equation

HRID 407331 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10](=[C:13](Cl)[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=[O:21])=[CH:16][CH:15]=1)[C:11]#[N:12].[OH2:24].[NH2:25][NH2:26]>C(O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:13]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:21])=[O:24])=[CH:16][CH:15]=2)=[N:26][NH:25][C:11]=1[NH2:12]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86608760HCID 86608760, compound

Product 1

HCID 178509111HCID 178509111, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The 2-benzothiazol-2-yl-3-chloro-3-(4-nitrophenyl)-acrylonitrile (500 mg, 1.46 mmol) prepared above and hydrazine hydrate (150 mg, 3 mmol) were refluxed in ethanol (15 mL) for 6 hrs. The solvent was evaporated and the residue was purified by flash column chromatography eluting with CH2Cl2:MeOH=9:1 to yield 182 mg (37%) of the title compound as a yellow solid. MS (m/z, ES+): 338.04 (M+1, 100%).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash column chromatography
  3. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-9fba245e81414446b2ae59b37ea1e956
Source dataset
uspto-grants-2014_06
Patent number
US08754233B2

Reaction notes

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