Hydrochloric Acid → HCID 13559523, compound

HRID 638587Notes

Reaction equation

HRID 638587 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][C:6]1[C:7]2[N:8]([N:19]=[CH:20][N:21]=2)[C:9](N)=[N:10][C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:2].N([O-])=O.[Na+].[ClH:26]>O>[Cl:26][C:9]1[N:8]2[N:19]=[CH:20][N:21]=[C:7]2[C:6]([CH2:5][CH2:4][O:3][CH2:1][CH3:2])=[C:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 55784BemitradineHCID 23668193Sodium Nitrite

Product 1

HCID 13559523HCID 13559523, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

A solution containing 100.8 g of 8-(2-ethoxyethyl)-7-phenyl[1,2,4]triazolo[1,5-c]pyrimidin-5-amine (0.36 moles) dissolved in 600 ml of concentrated hydrochloric acid and 420 ml. of water is cooled to 3° C. with constant stirring. To the cooled solution is added (below the surface of the solution) a mixture containing 54 g. of sodium nitrite (0.72 moles) in 75 ml of water over a period of fifteen minutes. The reaction mixture is stopped and stirred in an ice-bath for 0.5 hour and then stirred at room temperature for one hour. To the reaction mixture is added 150 ml of water and the resulting mixture is allowed to remain overnight at room temperature. A precipitate formed and the mixture is filtered and the precipitate is washed with water and dried yielding a crude product. The crude product is recrystallized from diethylether yielding 5-chloro-8-(2-ethoxyethyl)-7-phenyl[1,2,4]triazolo[1,5-c]pyrimidine represented by the structural formula ##STR18## as a white solid having a melting point of 134°-135° C. and the following elemental analysis:

Workup

  1. additionTo the cooled solution is added (below the surface of the solution) a mixture
  2. additioncontaining 54 g
  3. stirringstirred at room temperature for one hour
  4. waitto remain overnight at room temperature
  5. customA precipitate formed
  6. filtrationthe mixture is filtered
  7. washthe precipitate is washed with water
  8. customdried
  9. customyielding a crude product
  10. customThe crude product is recrystallized from diethylether

Sources & evidence

ORD record
ord-fae3ea76635945f8ba8228880b49f2bd
Source dataset
uspto-grants-1985_12
Patent number
US04562192

Reaction notes

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