tert-Butyl carbazate → HCID 67024448, compound

HRID 389096Notes

Reaction equation

HRID 389096 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]([CH3:18])([CH3:17])[C:14]([OH:16])=O)=[CH:4][CH:3]=1.[C:19]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])(=[O:22])[NH:20][NH2:21]>C(#N)C>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([O:12][C:13]([CH3:18])([CH3:17])[C:14]([NH:21][NH:20][C:19]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:16])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 70091tert-Butyl carbazateHCID 58244254HCID 58244254, compound

Product 1

HCID 67024448HCID 67024448, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-[(4-chloro-1-naphthyl)oxy]-2-methylpropanoic acid (6.66 g), WSC•monohydrochloride (6.0 g) and N,N-dimethylaminopyridine (200 mg) were dissolved in acetonitrile (70 ml), tert-butyl carbazate (4.0 g) was added thereto, followed by stirring at room temperature overnight. The solvent was concentrated under reduced pressure, water was added thereto, followed by extraction portionwise with chloroform, and the organic layer was washed with saturated brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (chloroform:methanol) to obtain tert-butyl 2-{2-[(4-chloro-1-naphthyl)oxy]-2-methylpropanoyl}hydrazinecarboxylate (6.10 g).

Workup

  1. concentrationThe solvent was concentrated under reduced pressure, water
  2. additionwas added
  3. extractionfollowed by extraction portionwise with chloroform
  4. washthe organic layer was washed with saturated brine
  5. dry with materialAfter drying over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel chromatography (chloroform:methanol)

Sources & evidence

ORD record
ord-689bb92b5cea4e8a9e5d68ed63c1a729
Source dataset
uspto-grants-2013_02
Patent number
US08377923B2

Reaction notes

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