Sodium Azide → 4-azido-3-ethoxy-N-ethylbenzamide

HRID 1717330Notes

Reaction equation

HRID 1717330 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([NH:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][CH2:14][CH3:15].N([O-])=O.[Na+].[N-:20]=[N+:21]=[N-].[Na+]>Cl>[N:1]([C:2]1[CH:12]=[CH:11][C:5]([C:6]([NH:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1[O:13][CH2:14][CH3:15])=[N+:20]=[N-:21]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 23668193Sodium NitriteHCID 633585494-amino-3-ethoxy-N-ethylbenzamide

Product 1

HCID 866298054-azido-3-ethoxy-N-ethylbenzamideYield 85%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 4-amino-3-ethoxy-N-ethylbenzamide (0.53 g) obtained in Example 131c) in 0.2N hydrochloric acid (12.5 ml) was added 1M aqueous sodium nitrite solution (2.5 ml) under ice-cooling, and the mixture was stirred for 2 hr. To the obtained reaction mixture was added an aqueous solution (5 ml) of sodium azide (0.17 g) under ice-cooling, and the mixture was stirred for 30 min. The reaction mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as a yellow oil (0.50 g, 85%).

Workup

  1. temperaturecooling
  2. customTo the obtained reaction mixture
  3. temperaturecooling
  4. stirringthe mixture was stirred for 30 min
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0c80758f338a4dcb9963d20409d2dab9
Source dataset
uspto-grants-2010_09
Patent number
US07803822B2

Reaction notes

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