Dimethylformamide → 2-(2-Azido-1-ethoxyethylideneamino)-5-nitrobenzophenone

HRID 867060Notes

Reaction equation

HRID 867060 reaction equation
Br[CH2:2][C:3](=[N:7][C:8]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11])[O:4][CH2:5][CH3:6].CN(C)C=O.[N-:30]=[N+:31]=[N-:32].[Na+].C(OCC)(=O)C>O>[N:30]([CH2:2][C:3](=[N:7][C:8]1[CH:21]=[CH:20][C:19]([N+:22]([O-:24])=[O:23])=[CH:18][C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11])[O:4][CH2:5][CH3:6])=[N+:31]=[N-:32]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 203172702-(2-Bromo-1-ethoxyethylideneamino)-5-nitrobenzophenone

Product 1

HCID 203172632-(2-Azido-1-ethoxyethylideneamino)-5-nitrobenzophenone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3.3 parts of 2-(2-bromo-1-ethoxyethylideneamino)-5-nitrobenzophenone produced in Step (1) in 15 parts by volume of dimethylformamide is added 0.5 part of sodium azide at a room temperature with stirring. After the stirring is continued for further 40 minutes. Ethyl acetate and water are added to the reaction mixture and shaken well. The ethyl acetate layer separated is washed with water and dried over anhydrous sodium sulfate. Evaporation of the solvent gives 2-(2-azido-1-ethoxyethylideneamino)-5-nitrobenzophenone as an oily substance. The product shows an absorption band at 2077 cm-1 due to N3 in an infrared absorption spectrum.

Workup

  1. stirringshaken well
  2. customThe ethyl acetate layer separated
  3. washis washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-0babb624e4964314aa8ad455c735fed5
Source dataset
uspto-grants-1978_07
Patent number
US04102881

Reaction notes

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