Sodium Azide → HCID 20291875, compound

HRID 1413342Notes

Reaction equation

HRID 1413342 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][CH:19]=[C:6]2[C:7]([N:9]([C:12]3[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=3)[C:10](=[O:11])[C:5]=12)=[O:8])([O-])=O.[N-:22]=[N+:23]=[N-].[Na+]>CS(C)=O>[N:1]([C:4]1[CH:21]=[CH:20][CH:19]=[C:6]2[C:7]([N:9]([C:12]3[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=3)[C:10](=[O:11])[C:5]=12)=[O:8])=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 20291882HCID 20291882, compound

Product 1

HCID 20291875HCID 20291875, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

13.5 g (0.047 mol) of 4-(3-nitrophthalimidyl)aniline and 3.4 g (0.051 mol) of sodium azide in 120 ml of dimethylsulphoxide are heated for 18 hours at 80° C. The reaction mixture is then concentrated in vacuo at 80° C. and diluted with 100 ml of water, the mixture is filtered with suction and the filter residue is washed with 20 ml of water and dried for 24 hours in a drying cabinet at 80° C./100 mm Hg. 13.1 g (100% of theory) of 4-(3-azidophthalimidyl)-aniline are obtained; melting point 176° C. (with decomposition). IR spectrum (KBr): 1780 and 1725 cm-1 (CO--N--CO); 2130 cm-1 (N3).

Workup

  1. concentrationThe reaction mixture is then concentrated in vacuo at 80° C.
  2. additiondiluted with 100 ml of water
  3. filtrationthe mixture is filtered with suction
  4. washthe filter residue is washed with 20 ml of water
  5. customdried for 24 hours in a drying cabinet at 80° C./100 mm Hg

Sources & evidence

ORD record
ord-4cd9351f68b141c885efd30a05648e8d
Source dataset
uspto-grants-1981_02
Patent number
US04250096

Reaction notes

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