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

HRID 387846

반응식

HRID 387846 반응식
[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

참가 물질

7

반응물 4

HCID 8857Ethyl Acetate2회HCID 14798Sodium HydroxideHCID 182112-Bromo-5-nitrothiazoleHCID 229368096,7-Dimethoxyquinoline-4(1H)-thione

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0cde1c2d547b47779348d45db479b3da
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372981B2

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