Ethyl Acetate → 6,7-Dimethoxy-4-(5-nitrothiazol-2-ylsulfanyl)quinoline

HRID 387846

反応式

HRID 387846 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[NH:9][CH:8]=[CH:7][C:6]2=[S:15].Br[C:17]1[S:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][N:21]=1.C(OCC)(=O)C.[OH-].[Na+]>CN(C)C=O.CCCCCC>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[S:15][C:17]1[S:18][C:19]([N+:22]([O-:24])=[O:23])=[CH:20][N:21]=1

参加物

7

反応物 4

HCID 8857Ethyl Acetate2 回HCID 14798Sodium HydroxideHCID 182112-Bromo-5-nitrothiazoleHCID 229368096,7-Dimethoxyquinoline-4(1H)-thione

生成物 1

HCID 229367196,7-Dimethoxy-4-(5-nitrothiazol-2-ylsulfanyl)quinoline収率 49%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8058Hexane溶媒

実験手順

After suspending 6,7-dimethoxy-1H-quinoline-4-thione (2.21 g, 10.0 mmol) in dimethylformamide (30 ml), 2-bromo-5-nitrothiazole (2.30 g, 11.0 mmol) was added at 0° C., and then the mixture was stirred at room temperature for 1 hour. The reaction solution was distributed between ethyl acetate and 1N aqueous sodium hydroxide, the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent-ethyl acetate:hexane=3:1), and the fraction containing the target substance was concentrated, suspended in ethyl acetate and diluted with hexane, after which the crystals were filtered out, washed with hexane and then blow-dried to obtain the title compound (1.70 g, 4.87 mmol, 49%) as light yellow crystals.

後処理

  1. additionwas added at 0° C.
  2. washthe organic layer was washed with water and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationthe drying agent was filtered off
  5. distillationthe filtrate was distilled off under reduced pressure
  6. customThe obtained crude product
  7. additionthe fraction containing the target substance
  8. concentrationwas concentrated
  9. additiondiluted with hexane
  10. filtrationafter which the crystals were filtered out
  11. washwashed with hexane
  12. customblow-dried

出典と根拠

ORDレコード
ord-0cde1c2d547b47779348d45db479b3da
出典データセット
uspto-grants-2013_02
特許番号
US08372981B2

関連ノート

読み込み中…