Sodium Bicarbonate → 2-(4-chlorophenyl)-4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-((4-chlorophenoxy)methyl]-4,5-dihydro-1H-imidazole

HRID 52310노트

반응식

HRID 52310 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[NH:20])[NH:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C(=O)(O)[O-:22].[Na+].BrCC(=O)[CH2:29][C:30]1C=CC=C[C:31]=1[O:36][C:37]1[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=1>CC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([C:10]3[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:17])=[O:18])=[CH:12][CH:11]=3)[CH2:29][C:30]([OH:22])([CH2:31][O:36][C:37]3[CH:42]=[CH:41][C:40]([Cl:43])=[CH:39][CH:38]=3)[N:20]=2)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 229980221-Bromo-3-[(4-chlorophenoxy)phenyl]-2-propanoneHCID 1785047964-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide

생성물 1

HCID 106487922-(4-chlorophenyl)-4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-((4-chlorophenoxy)methyl]-4,5-dihydro-1H-imidazole수율 35.5%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a mixture of 4-chloro-N-[4-(methylsulfonyl)phenyl]benzenecarboximidamide (Example 1, Step 1) (1 g, 3.24 mmol) and sodium bicarbonate (550 mg, 6.5 mmol) in acetone (100 mL), 1-bromo-3-[(4-chlorophenoxy)phenyl]-2-propanone from Step 2 (1.5 g, 5.8 mmol) was added. After heating to reflux for 24 hours, the reaction mixture was filtered, washed with acetone and concentrated in vacuo. The crude mixture (2.5 g) was chromatographed (silica gel, toluene/ethyl acetate, 1/1) to give 2-(4-chlorophenyl)-4-hydroxy-1-[4-(methylsulfonyl)phenyl]-4-[(4-chlorophenoxy)methyl]-4,5-dihydro-1H-imidazole (565 mg, 35%) as a white solid.

후처리

  1. additionwas added
  2. temperatureAfter heating
  3. temperatureto reflux for 24 hours
  4. filtrationthe reaction mixture was filtered
  5. washwashed with acetone
  6. concentrationconcentrated in vacuo
  7. customThe crude mixture (2.5 g) was chromatographed (silica gel, toluene/ethyl acetate, 1/1)

출처 및 근거

ORD 기록
ord-3b18c73141bd4612966010345a640184
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05616601

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