p-Toluenesulfonic acid → HCID 178498285, 화합물

HRID 349496

반응식

HRID 349496 반응식
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:12][O:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([NH2:23])[CH:16]=1.[Cl:25][C:26]1[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=1[F:34])[C:29]#[N:30].C([O-])(O)=O.[Na+]>>[CH3:12][O:13][C:14](=[O:24])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[C:17]([NH:23][C:29](=[NH:30])[C:28]2[CH:31]=[CH:32][C:33]([F:34])=[C:26]([Cl:25])[CH:27]=2)[CH:16]=1

참가 물질

5

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 1455253-Chloro-4-fluorobenzonitrileHCID 516892Sodium BicarbonateHCID 2734814Methyl 3-Amino-4-methoxybenzoate

생성물 1

HCID 178498285HCID 178498285, 화합물수율 45%

반응 조건

온도
160 °C

실험 절차

Anhydrous p-toluene sulfonic acid (10 g, 52.57 mmol) was melted at 120° C. and 3-amino-4-methoxy benzoic acid methyl ester (3.88 g, 21.44 mmol) obtained in step 1 of Preparation Example 1 and 3-chloro-4-fluorobenzonitrile (5.0 g, 32.14 mol) were added thereto and stirred at 160° C. for 8 hours. The resulting solution was cooled to room temperature and the reaction was stopped by adding NaHCO3 thereto. The resulting mixture was extracted with ethyl acetate, the extract was dried over MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (3.24 g, 9.62 mmol) in a yield of 45%.

후처리

  1. additionwere added
  2. temperatureThe resulting solution was cooled to room temperature
  3. extractionThe resulting mixture was extracted with ethyl acetate
  4. dry with materialthe extract was dried over MgSO4
  5. concentrationconcentrated under a reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-0f3630fd6bd54e7a832327e814aa6609
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07179832B2

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