2-Chloroethyl methyl ether → 6-(4-chlorobenzoyl)-4-(3-chlorophenyl)-1-(2-methoxyethyl)-2(1H)-quinolinone

HRID 1739832ノート

反応式

HRID 1739832 の反応式
[H-].[Na+].[Cl:3][C:4]1[CH:29]=[CH:28][C:7]([C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[NH:16][C:15](=[O:20])[CH:14]=[C:13]3[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)=[O:9])=[CH:6][CH:5]=1.[CH3:30][O:31][CH2:32][CH2:33]Cl>CS(C)=O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:8]([C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]([CH2:33][CH2:32][O:31][CH3:30])[C:15](=[O:20])[CH:14]=[C:13]3[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=2)=[O:9])=[CH:28][CH:29]=1

参加物

5

反応物 3

HCID 123162-Chloroethyl methyl etherHCID 24758Sodium hydrideHCID 155243306-(4-chlorobenzoyl)-4-(3-chlorophenyl)-2(1H)-quinolinone

生成物 1

HCID 218374826-(4-chlorobenzoyl)-4-(3-chlorophenyl)-1-(2-methoxyethyl)-2(1H)-quinolinone収率 36%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Sodium hydride (601 g) was added portionwise under N2 flow to a solution of interm. (9-d) (15 g) in dimethyl sulfoxide (200 ml). The mixture was stirred at room temperature for 30 minutes. 2-Chloroethyl methyl ether (25.2 ml) was added. The mixture was stirred at 50° C. for 72 hours, poured out on ice and extracted with ethyl acetate. The organic layer was separated, washed with water, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate 70/30). The pure fractions were collected and the solvent was evaporated, yielding 6.2 g (36%) of 6-(4-chlorobenzoyl)-4-(3-chlorophenyl)-1-(2-methoxyethyl)-2(1H)-quinolinone (interm. 9-e).

後処理

  1. stirringThe mixture was stirred at 50° C. for 72 hours
  2. additionpoured out on ice
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: cyclohexane/ethyl acetate 70/30)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated

出典と根拠

ORDレコード
ord-a68cd66e68bb448b8df98e3623628a01
出典データセット
uspto-grants-1999_10
特許番号
US05968952

反応ノート

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