tert-Butyl carbazate → tert-butyl N-(2-methyl-6-nitro-phenyl)-hydrazino-carboxylate

HRID 222865Notes

Reaction equation

HRID 222865 reaction equation
F[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12]([O:16][C:17]([NH:19][NH2:20])=[O:18])([CH3:15])([CH3:14])[CH3:13]>CS(C)=O>[CH3:8][C:7]1[CH:6]=[CH:5][CH:4]=[C:3]([N+:9]([O-:11])=[O:10])[C:2]=1[N:19]([C:17]([O:16][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:18])[NH2:20]

Participants

4

Reactant 2

HCID 70091tert-Butyl carbazateHCID 134709572-Fluoro-1-methyl-3-nitrobenzene

Product 1

HCID 68969283tert-butyl N-(2-methyl-6-nitro-phenyl)-hydrazino-carboxylateYield 80%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 250 mg of 2-fluoro-3-methyl-nitrobenzene in 5 mL of DMSO are added 1.065 g of commercial tert-butoxycarbonylhydrazine (5 equivalents). The whole is brought to 100° C. for 10 min under microwave heating. The medium is hydrolyzed and then extracted with ethyl acetate several times. The organic phases are collected, dried on magnesium sulfate, filtered and evaporated under reduced pressure leading to a residue which is purified by chromatography on silica gel (cyclohexane/ethyl acetate: 80/20). 342 mg of product corresponding to the expected product are obtained.

Workup

  1. temperatureheating
  2. extractionextracted with ethyl acetate several times
  3. customThe organic phases are collected
  4. customdried on magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customis purified by chromatography on silica gel (cyclohexane/ethyl acetate: 80/20)

Sources & evidence

ORD record
ord-0f4902de3d8b4c33b3b891bd80e88913
Source dataset
uspto-grants-2012_06
Patent number
US08207373B2

Reaction notes

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