Hydrochloric Acid → HCID 178481939, compound

HRID 1612572Notes

Reaction equation

HRID 1612572 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([F:10])([F:9])[F:8])=[CH:5][C:4]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH2:18])=[C:14]([NH2:19])[CH:13]=2)=[N:3]1.Cl.[N:21]([O-])=O.[Na+]>O>[CH3:1][N:2]1[C:6]([C:7]([F:9])([F:10])[F:8])=[CH:5][C:4]([O:11][C:12]2[CH:17]=[CH:16][C:15]3[N:18]=[N:21][NH:19][C:14]=3[CH:13]=2)=[N:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 19775932HCID 19775932, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178481939HCID 178481939, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

The o-phenylenediamine obtained in step B (1.0 g,3.7 mmol) in water (20 cm3) was treated with concentrated hydrochloric acid (1.7 cm3) at room temperature. After stirring for 15 minutes more water (10 cm3) was added and the mixture cooled in an ice/salt bath to ~0° C. A solution of sodium nitrite (0.544 g, 7.9 mmol) in water (5.5 cm3) was added dropwise, with stirring, maintaining the temperature at ≤0° C. When the addition was complete the reaction mixture was stirred at 0° C. for 30 minutes and then at room temperature for a further 2 hours. The mixture was extracted several times with ethyl acetate and the combined extracts washed with water, dried (MgSO4) and evaporated leaving 6-(1-methyl-5-trifluoromethyl-1H-pyrazol-3-yloxy)benzotriazole as a buff solid m.p. 129°-131° C.

Workup

  1. additionwas added
  2. temperaturethe mixture cooled in an ice/salt bath to ~0° C
  3. temperaturemaintaining the temperature at ≤0° C
  4. additionWhen the addition
  5. stirringwas stirred at 0° C. for 30 minutes
  6. extractionThe mixture was extracted several times with ethyl acetate
  7. washthe combined extracts washed with water
  8. dry with materialdried (MgSO4)
  9. customevaporated

Sources & evidence

ORD record
ord-427192ee3611484289bcf1c26195b750
Source dataset
uspto-grants-1993_03
Patent number
US05190574

Reaction notes

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