Tetrahydrofuran → HCID 57901783, compound

HRID 1851373Notes

Reaction equation

HRID 1851373 reaction equation
[Cl:1][C:2]1[C:10]2[C:5](=[C:6]([N+:11]([O-])=O)[CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:14][O:15][CH3:16])[C:3]=1[C:17]1[S:18][CH:19]=[CH:20][N:21]=1.O1CCCC1.O.NN>O.O.O.O.O.O.[Fe](Cl)(Cl)Cl.CO>[Cl:1][C:2]1[C:10]2[C:5](=[C:6]([NH2:11])[CH:7]=[CH:8][CH:9]=2)[N:4]([CH2:14][O:15][CH3:16])[C:3]=1[C:17]1[S:18][CH:19]=[CH:20][N:21]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 24654Hydrazine hydrate (1:1)HCID 57901680HCID 57901680, compound

Product 1

HCID 57901783HCID 57901783, compoundYield 91.8%

Reagents, catalysts & solvents 2

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-chloro-1-(methoxymethyl)-7-nitro-2-(1,3-thiazol-2-yl)-1H-indole (0.30 g), iron(III) chloride hexahydrate (15 mg), activated carbon (0.15 g), tetrahydrofuran (6 mL) and methanol (6 mL) was heated under reflux for 20 min. To the reaction mixture was added hydrazine monohydrate (0.27 g) while heating under reflux. The reaction mixture was heated under reflux for 2 hr, filtrated, and the filtrate was concentrated. The residue was dissolved in ethyl acetate, washed with saturated brine, dried (MgSO4) and concentrated to give the title compound (0.25 g, yield 91%) as a yellow oil.

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. dissolutionThe residue was dissolved in ethyl acetate
  10. washwashed with saturated brine
  11. dry with materialdried (MgSO4)
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-2eb0065c9aa74d62b1a72c6f9e628ede
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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