Sodium Azide → HCID 20291878, compound

HRID 1413340Notes

Reaction equation

HRID 1413340 reaction equation
[N+:1]([C:4]1[CH:21]=[CH:20][CH:19]=[C:6]2[C:7]([N:9]([CH:12]3[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]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]([CH:12]3[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]3)[C:10](=[O:11])[C:5]=12)=[O:8])=[N+:22]=[N-:23]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 20291883HCID 20291883, compound

Product 1

HCID 20291878HCID 20291878, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 2.9 g (0.01 mol) of 4-(3-nitrophthalimidyl)-cyclohexanol and 0.9 g (0.013 mol) of sodium azide in 20 ml of dimethylsulphoxide is stirred for 6 hours at 80° C. and then evaporated in vacuo at the same temperature. The residue is diluted with 20 ml of water. The product which has separated out is filtered off with suction, washed with 5 ml of water and dried for 24 hours at 80° C. in a drying cabinet. 2.6 g (91% of theory) of 4-(3-azidophthalimidyl)-cyclohexanol are obtained; melting point 155° C. (with decomposition). IR spectrum (KBr): 1775 cm-1 and 1710 cm-1 (CO--N--CO); 2130 cm-1 (N3).

Workup

  1. customevaporated in vacuo at the same temperature
  2. additionThe residue is diluted with 20 ml of water
  3. customThe product which has separated out
  4. filtrationis filtered off with suction
  5. washwashed with 5 ml of water
  6. customdried for 24 hours at 80° C. in a drying cabinet

Sources & evidence

ORD record
ord-03307c152d0b4dd785feb941262df960
Source dataset
uspto-grants-1981_02
Patent number
US04250096

Reaction notes

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