Hydrochloric Acid → HCID 178418385, compound

HRID 2413790Notes

Reaction equation

HRID 2413790 reaction equation
Cl[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([N+:9]([O-])=O)[CH:3]=1.Cl.[N:13]([O-])=O.[Na+].C(NC1C=CC(O)=CC=1)(=O)C.C(=O)(O)[O-].[Na+].[OH-].[Na+]>CCOCC.O>[NH:9]1[C:4]2[CH:3]=[CH:2][CH:8]=[CH:7][C:5]=2[N:6]=[N:13]1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 1983AcetaminophenHCID 69794-Chloro-2-nitroanilineHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 23668193Sodium Nitrite

Product 1

HCID 178418385HCID 178418385, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a cooled (0°-5° C.), well stirred suspension of 4-chloro-2-nitroaniline, 34.4 g. (0.2 mole) in 80 ml. of concentrated hydrochloric acid was added, dropwise, 18.0 g. (0.26 mole) of sodium nitrite in 10 ml. of water. The addition required approximately 30 minutes. After the addition was complete, the reaction mixture was filtered and the filtrate placed in an addition funnel containing approximately 100 g. of crushed ice. This solution was used immediately in the next step. The solution was added, dropwise, over 30 minutes to a well stirred suspension of 30.2 g. (0.2 mole) of p-acetamidophenol in 600 ml. of water containing 60 g. of sodium bicarbonate and 8 g. sodium hydroxide. The addition took about 20-30 minutes. The reaction was run most conveniently in a large beaker and small portions of ether were added to reduce foaming. The mixture was stirred for two hours and the dark red azo dye was collected by filtration and washed with a little water. The wet filter cake was suspended in 2,000 ml. of 5% sodium hydroxide and stirred well under nitrogen for 30 minutes. While maintaining a nitrogen atmosphere, 140 g. of Na2S2O4 was added in portions over one hour. The mixture was then boiled for one hour, cooled and filtered under nitrogen. The filtrate was acidified, under nitrogen, to a pH of 5. The yellow-grey precipitate was collected by filtration under nitrogen and dried in a vacuum desiccator to give 20 g. (38% yield) crude benzotriazole.

Workup

  1. temperatureTo a cooled
  2. additionThe addition required approximately 30 minutes
  3. additionAfter the addition
  4. filtrationthe reaction mixture was filtered
  5. customthe filtrate placed in an addition funnel
  6. additioncontaining approximately 100 g
  7. additionThe solution was added
  8. additionsuspension of 30.2 g
  9. additionThe addition
  10. waittook about 20-30 minutes
  11. additionwere added
  12. stirringThe mixture was stirred for two hours
  13. filtrationthe dark red azo dye was collected by filtration
  14. washwashed with a little water
  15. stirringof 5% sodium hydroxide and stirred well under nitrogen for 30 minutes
  16. temperatureWhile maintaining a nitrogen atmosphere, 140 g
  17. additionof Na2S2O4 was added in portions over one hour
  18. waitThe mixture was then boiled for one hour
  19. temperaturecooled
  20. filtrationfiltered under nitrogen
  21. filtrationThe yellow-grey precipitate was collected by filtration under nitrogen
  22. customdried in a vacuum desiccator
  23. customto give 20 g

Sources & evidence

ORD record
ord-62d0a98823e64199bb07e39492b7eb8f
Source dataset
uspto-grants-1988_01
Patent number
US04719248

Reaction notes

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