Hydrazine hydrate (1:1) → HCID 59759144, compound

HRID 914316Notes

Reaction equation

HRID 914316 reaction equation
[C:1]([O:5][C:6](=[O:35])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:21][C:20]=2[N+:32]([O-])=O)[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].O.NN>CO.[Fe](Cl)Cl>[C:1]([O:5][C:6](=[O:35])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([CH2:16][CH2:17][O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)=[CH:21][C:20]=2[NH2:32])[N:15]=1)([CH3:9])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 59759157HCID 59759157, compound

Product 1

HCID 59759144HCID 59759144, compoundYield 79.6%

Reagents, catalysts & solvents 2

HCID 24458Ferrous ChlorideCatalystHCID 887MethanolSolvent

Procedure

2-[(4-{2-[(4′-Fluoro-3-nitrobiphenyl-4-yl)oxy]ethyl}-1,3-thiazol-2-yl)thio]-2-methylpropionic acid tert-butyl ester (2.0 g) obtained in Example 97-2 was dissolved in methanol (20 mL), a catalytic amount of iron chloride (III) (62 mg), activated carbon (1.0 g) and hydrazine monohydrate (580 mg) were successively added, and the mixture was heated under reflux for 3 hr. The mixture was filtered through celite, methanol was evaporated under reduced pressure, and the residue was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (1.5 g).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 3 hr
  3. filtrationThe mixture was filtered through celite, methanol
  4. customwas evaporated under reduced pressure
  5. extractionthe residue was extracted with ethyl acetate
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c4a45386083b4a6fb570832e27b95b45
Source dataset
uspto-grants-2011_09
Patent number
US08026370B2

Reaction notes

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