tert-Butyl carbazate → Carbonazidic acid, 1,1-dimethylethyl ester

HRID 244926Notes

Reaction equation

HRID 244926 reaction equation
[C:1]([O:5][C:6](=[O:9])[NH:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].[N:10]([O-])=O.[Na+]>C(O)(=O)C.O>[C:6]([N:7]=[N+:8]=[N-:10])(=[O:9])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 70091tert-Butyl carbazateHCID 23668193Sodium Nitrite

Product 1

HCID 61256Carbonazidic acid, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

25 g (0.19 mol) of t-butylcarbazate was dissolved in 80 mL of acetic acid and 160 mL of water, and 15 g (0.22 mol) of sodium nitrite was added in small portions under cooling with ice. The reaction solution was stirred for 30 minutes under cooling with ice and extracted with 250 ml of diisopropyl ether. The organic layer was washed with 200 mL of saturated aqueous sodium hydrogen carbonate twice and with 100 mL of saturated aqueous sodium chloride once successively, dried over anhydrous sodium sulfate and filtered to give a solution of t-butyl carbonazidate in diethyl ether

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice
  3. extractionextracted with 250 ml of diisopropyl ether
  4. washThe organic layer was washed with 200 mL of saturated aqueous sodium hydrogen carbonate twice
  5. dry with materialwith 100 mL of saturated aqueous sodium chloride once successively, dried over anhydrous sodium sulfate
  6. filtrationfiltered

Sources & evidence

ORD record
ord-34df3a08cffc41cbaef113d4e79951ea
Source dataset
uspto-grants-2014_02
Patent number
US08658686B2

Reaction notes

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