Sodium Azide → HCID 20291873, compound

HRID 1413350Notes

Reaction equation

HRID 1413350 reaction equation
[CH2:1]([CH:3]([N:17]1[C:21](=[O:22])[C:20]2=[C:23]([N+:27]([O-])=O)[CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:30])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([CH3:16])([CH3:15])[CH2:13][OH:14])[CH3:2].[N-:31]=[N+:32]=[N-].[Na+]>CS(C)=O>[CH2:1]([CH:3]([N:17]1[C:21](=[O:22])[C:20]2=[C:23]([N:27]=[N+:31]=[N-:32])[CH:24]=[CH:25][CH:26]=[C:19]2[C:18]1=[O:30])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([CH3:16])([CH3:15])[CH2:13][OH:14])[CH3:2]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 20291872HCID 20291872, compound

Product 1

HCID 20291873HCID 20291873, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 20.9 g (0.05 mol) of N-(1-ethyl-10,10-dimethyl-11-hydroxyundecyl)-3-nitrophthalimide and 3.55 g (0.055 mol) of sodium azide in 100 ml of dimethylsulphoxide is stirred for 24 hours at 80° C. The solution is evaporated in vacuo and the residue is diluted with 300 ml of water. The resulting emulsion is extracted with twice 100 ml of diethyl ether. The ether extracts are first dried with anhydrous sodium sulphate, and then evaporated. 14.7 g (71% of theory) of N-(1-ethyl-10,10-dimethyl-11-hydroxyundecyl)-3-azidophthalimide are obtained in the form of a viscous oil which cannot be distilled.

Workup

  1. customThe solution is evaporated in vacuo
  2. additionthe residue is diluted with 300 ml of water
  3. extractionThe resulting emulsion is extracted with twice 100 ml of diethyl ether
  4. dry with materialThe ether extracts are first dried with anhydrous sodium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-1362b1f57180400dbdae86dd83264122
Source dataset
uspto-grants-1981_02
Patent number
US04250096

Reaction notes

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