Sodium Azide → HCID 20317279, compound

HRID 867057Notes

Reaction equation

HRID 867057 reaction equation
Br[CH2:2][C:3](=[N:7][C:8]1[CH:21]=[CH:20][C:19]([Cl:22])=[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-:23]=[N+:24]=[N-:25].[Na+]>CN(C)C=O>[N:23]([CH2:2][C:3](=[N:7][C:8]1[CH:21]=[CH:20][C:19]([Cl:22])=[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+:24]=[N-:25]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 20317273HCID 20317273, compound

Product 1

HCID 20317279HCID 20317279, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

to a solution of 3.8 parts of 2-(2-bromo-1-ethoxyethylideneamino)-5-chlorobenzophenone produced in Step (1) in 30 parts by volume of dimethylformamide is added 0.72 part of sodium azide. The mixture is heated at 80° C. for 10 minutes, and is poured into 60 parts by volume of ice water. The resulting oily precipitate is extracted with ethyl acetate. Ethyl acetate layer is washed with water and dried over anhydrous sodium sulfate. After evaporation of the solvent, 2-(2-azido-1-ethoxyethylideneamino)-5-chlorobenzophenone is obtained quantitatively as an oily substance. The product shows an absorption band at 2100 cm-1 due to N3 in an infrared absorption spectrum.

Workup

  1. extractionThe resulting oily precipitate is extracted with ethyl acetate
  2. washEthyl acetate layer is washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter evaporation of the solvent

Sources & evidence

ORD record
ord-e0be6f5dda81497e87d652186ef8964b
Source dataset
uspto-grants-1978_07
Patent number
US04102881

Reaction notes

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