Sulfuryl chloride → HCID 59292845, 화합물

HRID 1189897노트

반응식

HRID 1189897 반응식
S(Cl)([Cl:4])(=O)=O.[CH2:6]([O:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]([C:21]2[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[C:23]([O:29][CH3:30])[C:22]=2[F:31])=[C:15]2[C:20]=1[N:19]=[CH:18][CH:17]=[CH:16]2)=[O:10])[CH3:7]>CC#N>[CH2:6]([O:8][C:9]([C:11]1[CH:12]=[CH:13][C:14]([C:21]2[C:22]([F:31])=[C:23]([O:29][CH3:30])[CH:24]=[C:25]([O:27][CH3:28])[C:26]=2[Cl:4])=[C:15]2[C:20]=1[N:19]=[CH:18][CH:17]=[CH:16]2)=[O:10])[CH3:7]

참가 물질

4

반응물 2

HCID 24648Sulfuryl chlorideHCID 59292824HCID 59292824, 화합물

생성물 1

HCID 59292845HCID 59292845, 화합물수율 66.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
-20 °C

실험 절차

Sulfuryl chloride (75 μL, 0.93 mmol) was added dropwise to a cold (−20° C.) solution of 5-(2-fluoro-3,5-dimethoxy-phenyl)-quinoline-8-carboxylic acid ethyl ester (Step 176.3) (330 mg, 0.93 mmol) in CH3CN (6 mL). The reaction mixture was stirred for 10 min at −20° C., quenched by addition of a saturated solution of NaHCO3, and concentrated. The residue was diluted in EtOAc and a saturated solution of NaHCO3. The aqueous phase was separated and extracted with EtOAc. The combined organic layers were washed with H2O and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2) to provide 240 mg of the title compound as a white solid. Title compound: ESI-MS: 390.1 [M+H]+; tR=3.98 min (System 1); TLC: Rf=0.15 (Hex/EtOAc, 3:2).

후처리

  1. customquenched by addition of a saturated solution of NaHCO3
  2. concentrationconcentrated
  3. additionThe residue was diluted in EtOAc
  4. customThe aqueous phase was separated
  5. extractionextracted with EtOAc
  6. washThe combined organic layers were washed with H2O and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography (Hex/EtOAc, 3:2)

출처 및 근거

ORD 기록
ord-c4f20a8bc2d64e1292e19bcd271ccedc
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08674099B2

반응 노트

불러오는 중…