Imidazole → HCID 135840411, compound

HRID 1679167Notes

Reaction equation

HRID 1679167 reaction equation
[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[NH2:4].[N+:9]([O-])([O-])=O.[Na+].[NH:14]1[CH:18]=[CH:17][N:16]=[CH:15]1.C(=O)([O-])[O-].[Na+].[Na+]>Cl>[Cl:1][C:2]1[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=1[N:4]=[N:9][C:15]1[NH:14][CH:18]=[CH:17][N:16]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 72402-ChloroanilineHCID 10340Sodium CarbonateHCID 24268Sodium Nitrate

Product 1

HCID 135840411HCID 135840411, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Ice water (750 cc) and concentrated hydrochloric acid (250 cc) were stirred and cooled in an ice bath. Upon the addition of 2-chloroaniline (128.0 grams, 1.0 mole) to the cooled reaction mass, a white solid precipitated out. The resulting mixture was stirred at about 0°C as sodium nitrate (69.0 grams, 1.0 mole) was added in portions over a period of about 15 minutes. After the addition was complete the reaction mass was stirred for an additional 15 minutes after which 68.0 grams (1.0 mole) of imidazole were added. The reaction mass was stirred vigorously as anhydrous sodium carbonate (160.0 grams) was added. The mixture was stirred for 3 hours after which the orange crystals were filtered and washed with water. The damp crystals were mixed with dilute hydrochloric acid and stirred at room temperature for about one hour. The mixture was filtered and the insoluble material discarded. The filtrate was made basic with sodium carbonate. The yellow crystals of 2-((2-chlorophenyl)azo)-1H-imidazole was filtered off and washed with water. The product was recrystallized from ethanol. The proposed structure was confirmed by IR and NMR spectra. The melting point was 195°-196° C.

Workup

  1. temperaturecooled in an ice bath
  2. customto the cooled reaction mass
  3. customa white solid precipitated out
  4. additionwas added in portions over a period of about 15 minutes
  5. additionAfter the addition
  6. additionwere added
  7. additionwas added
  8. filtrationwere filtered
  9. washwashed with water
  10. additionThe damp crystals were mixed with dilute hydrochloric acid
  11. stirringstirred at room temperature for about one hour
  12. filtrationThe mixture was filtered
  13. filtrationThe yellow crystals of 2-((2-chlorophenyl)azo)-1H-imidazole was filtered off
  14. washwashed with water
  15. customThe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-b6f7760969654a44818e4f58edd663c7
Source dataset
uspto-grants-1978_03
Patent number
US04079130

Reaction notes

Loading…