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

HRID 2356021Notes

Reaction equation

HRID 2356021 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
  6. customThe concentrate was purified by flash column chromatography on silica gel with 1:0.5:98.5/methanol

Sources & evidence

ORD record
ord-807e3bfdf5ee4fb29ca3e2fc6e3e839e
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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