Sodium Azide → HCID 13559527, compound

HRID 638590Notes

Reaction equation

HRID 638590 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5]([CH2:11][CH2:12][OH:13])=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:3]=1.[N-:20]=[N+:21]=[N-:22].[Na+]>CS(C)=O.O>[C:14]1([C:4]2[N:3]3[N:20]=[N:21][N:22]=[C:2]3[N:7]3[N:8]=[CH:9][N:10]=[C:6]3[C:5]=2[CH2:11][CH2:12][OH:13])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 13559525HCID 13559525, compound

Product 1

HCID 13559527HCID 13559527, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution containing 27.4 g of 5-chloro-7-phenyl[1,2,4]triazolo[1,5-c]pyrimidine-8-ethanol (0.1 mole) dissolved in 250 ml of dimethylsulfoxide is added 13 g of sodium azide (0.2 mole). The resulting reaction mixture is stirred for 5 hours at a temperature of 65°-70° C. and then stirred overnight at room temperature. The reaction mixture is poured in water with stirring. A precipitate forms and the mixture is filtered and the precipitate is washed with water and dried yielding a crude product. The crude product is recrystallized from diethyl ether to yield 5-phenyltetrazolo[1,5-a][1,2,4]triazolo[1,5-c]pyrimidine-6-ethanol having the structural formula ##STR22## and the azido tautomer thereof as a white solid having a melting point of 110° C. and the following elemental analysis:

Workup

  1. customThe resulting reaction mixture
  2. stirringstirred overnight at room temperature
  3. stirringwith stirring
  4. filtrationA precipitate forms and the mixture is filtered
  5. washthe precipitate is washed with water
  6. customdried
  7. customyielding a crude product
  8. customThe crude product is recrystallized from diethyl ether

Sources & evidence

ORD record
ord-23945bc10da949cbabf11efcca4309b6
Source dataset
uspto-grants-1985_12
Patent number
US04562192

Reaction notes

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