Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate) → Ethyl 7-chloro-1-(2-chloroethyl)-1,4-dihydro-4-oxo-quinoline3-carboxylate

HRID 328570노트

반응식

HRID 328570 반응식
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][NH:9]2)=[CH:4][CH:3]=1.[H-].[Na+].S(O[CH2:31][CH2:32][Cl:33])(C1C=CC(C)=CC=1)(=O)=O>>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:17])[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:8][N:9]2[CH2:31][CH2:32][Cl:33])=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 6639Ethanol, 2-chloro-, 1-(4-methylbenzenesulfonate)HCID 24758Sodium hydrideHCID 345422Ethyl 7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylate

생성물 1

HCID 13174336Ethyl 7-chloro-1-(2-chloroethyl)-1,4-dihydro-4-oxo-quinoline3-carboxylate

반응 조건

온도
100 °C

실험 절차

To a mixture containing 23.4 g of ethyl 7-chloro-1,4-dihydro-4-oxoquinoline-3-carboxylate and 6.9 g of 65% sodium hydride was added 90g of 2-tosyloxyethyl chloride. The resulting mixture was heated at 100° C for 4 hours. After concentration to dryness, the residue was extracted with chloroform. The extract was washed with water, and dried over anhydrous sodium sulfate. The solvent was removed by the distillation to leave a solid which was recrystallized from ethanol to give ethyl 7-chloro-1-(2-chloroethyl)-1,4-dihydro-4-oxo-quinoline3-carboxylate, m.p. 207.5°-209.5° C.

후처리

  1. concentrationAfter concentration to dryness
  2. extractionthe residue was extracted with chloroform
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed by the distillation
  6. customto leave a solid which
  7. customwas recrystallized from ethanol

출처 및 근거

ORD 기록
ord-c04490d568ec45cd938521fcc59bae22
출처 데이터셋
uspto-grants-1977_04
특허 번호
US04017622

반응 노트

불러오는 중…