Hydrochloric Acid → HCID 135840411, compound

HRID 1833990Notes

Reaction equation

HRID 1833990 reaction equation
Cl.[Cl:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].[N:10]([O-])=O.[Na+].[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[N:5]=[N:10][C:15]1[NH:14][CH:18]=[CH:17][N:16]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 72402-ChloroanilineHCID 10340Sodium CarbonateHCID 23668193Sodium Nitrite

Product 1

HCID 135840411HCID 135840411, compoundYield 103.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 750 cubic centimeters (cc) of ice water and 250 cc of concentrated hydrochloric acid which was stirred and cooled to ~0° C was added 128.0 grams (1.0 mole) of 2-chloroaniline. Immediately a white solid formed. This mixture was stirred at ~0° C as 69.0 grams (1.0 mole) of sodium nitrite was added over a period of ~15 minutes. After the completion of the addition, the newly formed solution was stirred for ~15 minutes and 68.0 grams (1.0 mole) of imidazole was added. After a short period, 5.0 liters of water was added and the temperature was brought to ~0° C. To this mixture was slowly added with vigorous stirring 160.0 grams of anhydrous sodium carbonate and the mixture thereafter stirred at ~0° C for 3.0 hours. At the end of the period, the solution was filtered and the solid which was recovered was washed with water. The solids were thereafter mixed with dilute hydrochloric acid (200 cc of concentrated hydrochloric acid diluted to 2.0 liters) and stirred at room temperature for ~1.0 hour. The insolubles were removed by filtration and discarded. The filtrate was made basic with 140.0 grams of sodium carbonate and the crystals which formed were removed by filtration, washed with water and dried to give 213.5 grams of crude 2-((2-chlorophenyl)azo)imidazole melting at 173°-177° C.

Workup

  1. temperaturecooled to ~0° C
  2. customImmediately a white solid formed
  3. additionwas added over a period of ~15 minutes
  4. additionAfter the completion of the addition
  5. stirringthe newly formed solution was stirred for ~15 minutes
  6. waitAfter a short period
  7. customwas brought to ~0° C
  8. additionTo this mixture was slowly added
  9. stirringthe mixture thereafter stirred at ~0° C for 3.0 hours
  10. filtrationAt the end of the period, the solution was filtered
  11. customthe solid which was recovered
  12. washwas washed with water
  13. additionThe solids were thereafter mixed with dilute hydrochloric acid (200 cc of concentrated hydrochloric acid diluted to 2.0 liters)
  14. stirringstirred at room temperature for ~1.0 hour
  15. customThe insolubles were removed by filtration
  16. customthe crystals which formed
  17. customwere removed by filtration
  18. washwashed with water
  19. customdried

Sources & evidence

ORD record
ord-00eb2bcf763c47feaf136beeeaa5186a
Source dataset
uspto-grants-1978_01
Patent number
US04067973

Reaction notes

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