Sodium hydride → 1-[6-(1,3-Benzothiazol-2-yloxy)hexyl]-3-(3-pyridyl)-2-imidazolidinone

HRID 49261ノート

反応式

HRID 49261 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([N:7]2[CH2:11][CH2:10][NH:9][C:8]2=[O:12])[CH:2]=1.[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[S:24][C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=1>CN(C)C=O>[S:24]1[C:25]2[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=2[N:27]=[C:23]1[O:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:9]1[CH2:10][CH2:11][N:7]([C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[C:8]1=[O:12]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 148342041-(Pyridin-3-yl)imidazolidin-2-oneHCID 206365982-[(6-Bromohexyl)oxy]-1,3-benzothiazole

生成物 1

HCID 129864841-[6-(1,3-Benzothiazol-2-yloxy)hexyl]-3-(3-pyridyl)-2-imidazolidinone

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 1-(3-pyridyl)-2-imidazolidinone (0.11 g, 0.65 mmol) dissolved in 10 mL dimethylformamide cooled in an ice bath was added NaH (60% dispersion in mineral oil, 31.2 mg, 0.78 mmol). The mixture was stirred at room temperature for 30 minutes and then cooled in ice bath again. 2-[(6-Bromohexyl)oxy]-1,3-benzothiazole (0.20 g, 0.65 mmol) was added, and the mixture was stirred at room temperature for additional 4 hours. The reaction was quenched with MeOH, and the solvent was removed under vacuum. A saturated aqueous NH4Cl solution (5 mL) and dichloromethane (10 mL) were successively added to the residue. The dichloromethane layer was separated and dried over MgSO4, filtered, evaporated, and purified by column chromatography (ethyl acetate:MeOH=10:1) to give the product (i.e., Compound 4) as a white solid (0.14 g, 88%).

後処理

  1. temperaturecooled in an ice bath
  2. temperaturecooled in ice bath again
  3. stirringthe mixture was stirred at room temperature for additional 4 hours
  4. customThe reaction was quenched with MeOH
  5. customthe solvent was removed under vacuum
  6. additionA saturated aqueous NH4Cl solution (5 mL) and dichloromethane (10 mL) were successively added to the residue
  7. customThe dichloromethane layer was separated
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. custompurified by column chromatography (ethyl acetate:MeOH=10:1)

出典と根拠

ORDレコード
ord-e1fa68aed43a4cc0b57949ea7be6939a
出典データセット
uspto-grants-2004_03
特許番号
US06706739B2

反応ノート

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