Water → HCID 13559526, compound

HRID 638588Notes

Reaction equation

HRID 638588 reaction equation
Cl[C:2]1[N:7]2[N:8]=[CH:9][N:10]=[C:6]2[C:5]([CH2:11][CH2:12][O:13][CH2:14][CH3:15])=[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:3]=1.[N-:22]=[N+:23]=[N-:24].[Na+].O>CS(C)=O>[CH2:14]([O:13][CH2:12][CH2:11][C:5]1[C:6]2[N:7]([N:8]=[CH:9][N:10]=2)[C:2]2[N:3]([N:22]=[N:23][N:24]=2)[C:4]=1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 13559523HCID 13559523, compound

Product 1

HCID 13559526HCID 13559526, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution containing 30.2 g of 5-chloro-8-(2-ethoxyethyl)-7-phenyl[1,2,4]triazolo[1,5-c]pyrimidine (0.1 moles) dissolved in 200 ml of dimethylsulfoxide is added 20 g of sodium azide (0.3 moles). The resulting reaction mixture is heated to 65°-70° C. and then stirred for 5 hours. The reaction mixture is then stirred overnight at room temperature. The reaction mixture is then stirred into 1 liter of water and a precipitate forms. The mixture is filtered and the precipitate is washed with water and dried yielding a crude product. The crude product is chromatographed on silica gel and recrystallized from diethylether to yield 6-(2-ethoxyethyl)-5-phenyltetrazolo[1,5-a][1,2,4]triazolo[1,5-c]pyrimidine having the structural formula ##STR20## and the azido tautomer thereof as a white solid having a melting point of 114° C. and the following elemental analysis:

Workup

  1. customThe resulting reaction mixture
  2. temperatureis heated to 65°-70° C.
  3. stirringThe reaction mixture is then stirred overnight at room temperature
  4. filtrationThe mixture is filtered
  5. washthe precipitate is washed with water
  6. customdried
  7. customyielding a crude product
  8. customThe crude product is chromatographed on silica gel
  9. customrecrystallized from diethylether

Sources & evidence

ORD record
ord-c4d83a59c5af4a99a85a73c1ae2bb634
Source dataset
uspto-grants-1985_12
Patent number
US04562192

Reaction notes

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