Tetrahydrofuran → HCID 136060813, compound

HRID 1851366Notes

Reaction equation

HRID 1851366 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[S:17][N:16]=[CH:15][N:14]=1)=[CH:9]2)([O-])=O.O1CCCC1.O.NN>O.O.O.O.O.O.[Fe](Cl)(Cl)Cl.CO>[S:17]1[C:13]([C:10]2[NH:11][C:12]3[C:8]([CH:9]=2)=[CH:7][CH:6]=[CH:5][C:4]=3[NH2:1])=[N:14][CH:15]=[N:16]1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 136060830HCID 136060830, compound

Product 1

HCID 136060813HCID 136060813, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

A mixture of 7-nitro-2-(1,2,4-thiadiazol-5-yl)-1H-indole (0.41 g), iron(III) chloride hexahydrate (33 mg), activated carbon (0.33 g), tetrahydrofuran (12 mL) and methanol (6 mL) was heated under reflux for 20 min. To the reaction mixture was added hydrazine monohydrate (0.50 g) over 10 min while heating under reflux. The reaction mixture was heated under reflux for 2 hr, filtrated, and the filtrate was concentrated. The resulting crystals were washed with water, and dried to give the title compound (0.35 g, yield 94%) as colorless crystals. melting point>223° C. (decomposition).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 20 min
  3. temperaturewhile heating
  4. temperatureunder reflux
  5. temperatureThe reaction mixture was heated
  6. temperatureunder reflux for 2 hr
  7. filtrationfiltrated
  8. concentrationthe filtrate was concentrated
  9. washThe resulting crystals were washed with water
  10. customdried

Sources & evidence

ORD record
ord-bbe6f0ab8c1a44bebf51085346db0adf
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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