Triethylamine → N-(3-chloro-4-(3-chlorophenoxy)phenyl)picolinamide

HRID 38243

반응식

HRID 38243 반응식
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](Cl)=[O:9].CCN(CC)CC.[Cl:18][C:19]1[CH:20]=[C:21]([CH:23]=[CH:24][C:25]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=1)[NH2:22]>C(Cl)Cl>[Cl:18][C:19]1[CH:20]=[C:21]([NH:22][C:8](=[O:9])[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=2)[CH:23]=[CH:24][C:25]=1[O:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[CH:28]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 135033Picolinoyl Chloride HydrochlorideHCID 176055343-Chloro-4-(3-chlorophenoxy)aniline

생성물 1

HCID 42645239N-(3-chloro-4-(3-chlorophenoxy)phenyl)picolinamide수율 51%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

According to Scheme 3 Step 3: Picolinoyl chloride hydrochloride (1.52 mmol, 271 mg) and Et3N (3.05 mmol, 0.42 mL) were added sequentially to a solution of 3-chloro-4-(3-chlorophenoxy)aniline (1.02 mmol, 258 mg) in DCM (6 mL) at 0° C. The reaction mixture was stirred at room temperature for 2 hours. The organic phase was washed with a saturated solution of NaHCO3 and with brine, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel using cyclohexane/AcOEt (90:10) as eluent to afford N-(3-chloro-4-(3-chlorophenoxy)phenyl)picolinamide (0.52 mmol, 187 mg, 51%) as a white solid.

후처리

  1. washThe organic phase was washed with a saturated solution of NaHCO3 and with brine
  2. dry with materialwas dried over MgSO4
  3. filtrationwas filtered
  4. concentrationwas concentrated under reduced pressure
  5. customThe crude product was purified by flash chromatography over silica gel

출처 및 근거

ORD 기록
ord-4dd49d5ee1784637a7cfe86cc55f2823
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524726B2

연결된 노트

불러오는 중…