Hydrochloric Acid → 2-[(2-Chlorophenyl)thio]-1H-imidazole

HRID 1074203Notes

Reaction equation

HRID 1074203 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1.N([O-])=O.[Na+].[ClH:18]>C(O)(=O)C.O>[Cl:18][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[NH:10][CH:11]=[CH:12][N:13]=1

Participants

6

Reactant 3

HCID 313Hydrochloric Acid2×HCID 131782542-[(1H-Imidazol-2-yl)sulfanyl]anilineHCID 23668193Sodium Nitrite

Product 1

HCID 150775002-[(2-Chlorophenyl)thio]-1H-imidazoleYield 79%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 5.6 g (29.3 mmoles) of the product from Example 32 in 50 ml of 3N hydrochloric acid and 50 ml of glacial acetic acid (cooled in an ice bath), was added dropwise over 20 minutes, a solution of 2.0 g (29.3 mmoles) of sodium nitrite in 8 ml of water. After stirring for 10 minutes, the mixture was added to a cold solution of 8.7 g (80 mmoles) cuprous chloride in 80 ml of 6N hydrochloric acid. After stirring at room temperature for 5 hours, the mixture was concentrated and the residue made alkaline with ammonium hydroxide. The product was extracted with dichloromethane which was washed with saturated sodium chloride, dried and concentrated. The residue was dissolved in hot dichloromethane and filtered through silica gel using dichloromethane/ethyl acetate (1:1 by volume) as the eluent. The fractions containing the product were concentrated to give 4.9 g (79%) of the product which was crystallized from dichloromethane to give colorless rods, mp 138°-141° C.

Workup

  1. stirringAfter stirring at room temperature for 5 hours
  2. concentrationthe mixture was concentrated
  3. extractionThe product was extracted with dichloromethane which
  4. washwas washed with saturated sodium chloride
  5. customdried
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in hot dichloromethane
  8. filtrationfiltered through silica gel
  9. additionThe fractions containing the product
  10. concentrationwere concentrated

Sources & evidence

ORD record
ord-dc428a4422b740f6bce414cb22134259
Source dataset
uspto-grants-1990_11
Patent number
US04973599

Reaction notes

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