tert-Butyl carbazate → Tert-butyl 2-(4-(aminosulfonyl)-2-nitrophenyl)hydrazinecarboxylate

HRID 1785766Notes

Reaction equation

HRID 1785766 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11]C(C2C=CC(C3C=CC(F)=CC=3)=CC=2)=O)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:27]([O-:29])=[O:28].[C:30]([O:34][C:35](=[O:38])[NH:36][NH2:37])([CH3:33])([CH3:32])[CH3:31]>C(O)C.C(OCC)(=O)C>[NH2:11][S:8]([C:5]1[CH:6]=[CH:7][C:2]([NH:37][NH:36][C:35]([O:34][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:38])=[C:3]([N+:27]([O-:29])=[O:28])[CH:4]=1)(=[O:9])=[O:10]

Participants

5

Reactant 2

HCID 70091tert-Butyl carbazateHCID 102249074-Chloro-n-((4'-fluoro(1,1'-biphenyl)-4-yl)carbonyl)-3-nitrobenzenesulfonamide

Product 1

HCID 22730367Tert-butyl 2-(4-(aminosulfonyl)-2-nitrophenyl)hydrazinecarboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Example 1D (212 mg, 0.49 mmol) and tert-butylcarbazate (976 mg, 2.3 mmol) in ethanol (5 mL) was heated to reflux, stirred for 16 hours, diluted with ethyl acetate (50 mL), washed with water and brine, dried (MgSO4), filtered, and concentrated The concentrate was purified by flash column chromatography on silica gel with 1:0.5:98. 5/methanol:acetic acid:dichloromethane, then 2:0.5:97.5/methanol:acetic acid:dichloromethane to provide the desired product. MS (ESI(−)) m/e 331 (M−H)−.

Workup

  1. temperatureto reflux
  2. washwashed with water and brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated The concentrate
  6. customwas purified by flash column chromatography on silica gel with 1:0.5:98

Sources & evidence

ORD record
ord-7738d08d618640a88055853f71bf6e20
Source dataset
uspto-grants-2009_03
Patent number
US07504512B2

Reaction notes

Loading…