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

HRID 1504265Notes

Reaction equation

HRID 1504265 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-5cf183ac42b74409af2f400de8fe9d7e
Source dataset
uspto-grants-2015_12
Patent number
US09212348B2

Reaction notes

Loading…