Hydrazine hydrate (1:1) → HCID 18416009, compound

HRID 990973Notes

Reaction equation

HRID 990973 reaction equation
[C:1]([CH:9]1[S:13][C:12]2[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=2[C:10]1=O)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[NH2:20][NH2:21]>C(O)CCC>[C:2]1([C:1]2[C:9]3[S:13][C:12]4[CH:14]=[CH:15][CH:16]=[CH:17][C:11]=4[C:10]=3[NH:20][N:21]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 5131304HCID 5131304, compound

Product 1

HCID 18416009HCID 18416009, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-benzoylbenzo[b]thiophen-3(2H)-one (1.50 g, supplied by the Maybridge Chemical Company, Tintagel, England) hydrazine hydrate (0.3 ml) and butan-1-ol (50 ml) was boiled under reflux under nitrogen for 7.5 hours. The solvent was removed under reduced pressure and the residue was taken up in ethyl acetate, washed with water, dried, filtered and evaporated to give a solid which was purified by flash column chromatography on silica using toluene/ethyl acetate (7.5:1) as the mobile phase. Appropriate fractions were collected, combined and evaporated to give a solid which was triturated with ether, and filtered to give 3-phenyl-1H-[1]benzothieno[3,2-c]pyrazole, m.p. 236-238° C.

Workup

  1. temperatureunder reflux under nitrogen for 7.5 hours
  2. customThe solvent was removed under reduced pressure
  3. washwashed with water
  4. customdried
  5. filtrationfiltered
  6. customevaporated
  7. customto give a solid which
  8. customwas purified by flash column chromatography on silica
  9. customAppropriate fractions were collected
  10. customevaporated
  11. customto give a solid which
  12. customwas triturated with ether
  13. filtrationfiltered

Sources & evidence

ORD record
ord-528284ea33074d8997bec8c98bc16d57
Source dataset
uspto-grants-2002_10
Patent number
US06462036B1

Reaction notes

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