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

HRID 52310ノート

反応式

HRID 52310 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3b18c73141bd4612966010345a640184
出典データセット
uspto-grants-1997_04
特許番号
US05616601

反応ノート

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