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

HRID 1074203노트

반응식

HRID 1074203 반응식
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

참가 물질

6

반응물 3

HCID 313Hydrochloric Acid2회HCID 131782542-((1H-imidazol-2-yl)thio)anilineHCID 23668193Sodium Nitrite

생성물 1

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

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dc428a4422b740f6bce414cb22134259
출처 데이터셋
uspto-grants-1990_11
특허 번호
US04973599

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