Hydrochloric Acid → HCID 20211588, compound

HRID 1414362Notes

Reaction equation

HRID 1414362 reaction equation
[OH:1][C:2]1[C:7]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH3:9])=[CH:6][C:5]([CH3:16])=[CH:4][C:3]=1[N:17]1[N+:21]([O-])=[C:20]2[CH:23]=[C:24]([Cl:27])[CH:25]=[CH:26][C:19]2=[N:18]1.[OH-].[Na+].O.NN.Cl>O.COCCOCCOC>[OH:1][C:2]1[C:7]([CH:8]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH3:9])=[CH:6][C:5]([CH3:16])=[CH:4][C:3]=1[N:17]1[N:18]=[C:19]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:20]2=[N:21]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 21487206HCID 21487206, compound

Product 1

HCID 20211588HCID 20211588, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8150DiglymeSolvent

Conditions

Temperature
130 °C

Procedure

152 g (0.4 mol) of 2-(2-hydroxy-3-α-phenylethyl-5-methylphenyl)-6-chloro-benztriazole-1 oxide and 17.6 g (0.44 mol) of sodium hydroxide are introduced into 327 g of diethylene glycol dimethyl ether and the mixture is heated to 130° C, a little water distilling off azeotropically with the solvent. Exactly 12.0 g (0.24 mol) of hydrazine hydrate are passed in under the surface of the solution over the course of 11/2 hours while keeping the temperature between 133° and 135° C. In the course thereof, the water liberated is continuously removed by azeotropic distillation. After the addition is complete, the mixture is left to complete the reaction for about 1 hour at the same temperature and, as soon as the evolution of nitrogen stops, the resulting solution is cooled to 80° C and treated with 200 ml of cold water. About 53.7 g of 30% strength hydrochloric acid are then added dropwise at a regular rate until the mixture has a neutral reaction and it is cooled to about 40° C while stirring vigorously, whereupon the product crystallises out. The suspension is then diluted with 800 ml of water and filtered and the crude product is washed with a total of 300 ml of hot water. After drying in vacuo at 60°-70° C, 137.5 g of 2-(2-hydroxy-3-α-phenylethyl-5-methylphenyl)-5-chloro-benztriazole of 97% purity are obtained, which corresponds to a yield of 91.5% of theory. The melting point is 113°-115° C (the pure product melts between 115° and 119° C).

Workup

  1. customthe temperature between 133° and 135° C
  2. customIn the course thereof, the water liberated is continuously removed by azeotropic distillation
  3. additionAfter the addition
  4. waitthe mixture is left
  5. customthe reaction for about 1 hour at the same temperature
  6. temperaturethe resulting solution is cooled to 80° C
  7. customa neutral reaction and it
  8. temperatureis cooled to about 40° C
  9. customcrystallises out
  10. additionThe suspension is then diluted with 800 ml of water
  11. filtrationfiltered
  12. washthe crude product is washed with a total of 300 ml of hot water
  13. customAfter drying in vacuo at 60°-70° C

Sources & evidence

ORD record
ord-f3fdc20fe7e34feb991192e8d4326599
Source dataset
uspto-grants-1977_01
Patent number
US04001266

Reaction notes

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