Hydrazine hydrate (1:1) → HCID 178509112, compound

HRID 57277Notes

Reaction equation

HRID 57277 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]1O[CH:16]=[CH:17][CH:18]=1)[C:11]#[N:12].[OH2:20].[NH2:21][NH2:22]>CO>[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[O:20][CH:16]=[CH:17][CH:18]=2)=[N:22][NH:21][C:11]=1[NH2:12]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86608762HCID 86608762, compound

Product 1

HCID 178509112HCID 178509112, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 2-benzothiazol-2-yl-3-chloro-3-furan-2-ylacrylonitrile (480 mg, 1.7 mmol) prepared above and hydrazine hydrate (100 mg, 2 mmol) were refluxed in methanol (15 mL) for 3 hrs. The solvent was then evaporated and the residue was purified by flash column chromatography eluting with CH2Cl2:MeOH=9:1 to afford 130 mg of material. This was further purified by preparative TLC eluting with CH2Cl2:MeOH=9:1 to yield 23 mg (5%) of the title compound. MS (m/z, ES+): 283.0 (M+1, 100%).

Workup

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

Sources & evidence

ORD record
ord-b158fef65b59435cad20bf0f0c274631
Source dataset
uspto-grants-2016_09
Patent number
US09434720B2

Reaction notes

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