Sodium Iodide → HCID 22171013, 화합물

HRID 2376204노트

반응식

HRID 2376204 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:12]=[C:11]([CH2:22]OS(C)(=O)=O)[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[Na+].[I-:29]>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[N:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[N:12]=[C:11]([CH2:22][I:29])[CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

참가 물질

4

반응물 2

HCID 5238Sodium IodideHCID 23568903HCID 23568903, 화합물

생성물 1

HCID 22171013HCID 22171013, 화합물수율 97%

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

A stirred solution of methanesulfonic acid 5-(3,4-dichlorophenyl)-1-(4-methoxyphenyl)-1H-pyrazol-3-ylmethyl ester (8.80 g, 0.0206 mol) and NaI (4.64 g, 0.0309 mol) in acetone (175 mL) was refluxed for 90 min. The thick reaction slurry was cooled to rt, quenched with H2O (200 mL) and extracted with EtOAc (3×75 mL). The organic layer was dried with Na2SO4, filtered and concentrated to a dark oil. The crude oil was purified by column chromatography (silica gel, 85:15 hexane/EtOAc) to obtain 9.15 g (97%) of the title compound after two steps. HPLC: Rt=11.03 (Method E). MS (ES+): mass calculated for C17H13Cl2IN2O, 459.10; m/z found 460.9 [M+H]+. 1H NMR (400 MHz, CDCl3): 7.37 (d, J=2.0 Hz, 1H), 7.34 (d, J=8.3 Hz, 1H), 7.18 (d, J=8.8 Hz, 2H), 6.95 (dd, J=6.3, 2.0 Hz, 1H), 6.88 (d, J=9.1 Hz, 2H), 6.55 (s, 1H), 4.47 (s, 2H), 3.83 (s, 3H).

후처리

  1. customquenched with H2O (200 mL)
  2. extractionextracted with EtOAc (3×75 mL)
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated to a dark oil
  6. customThe crude oil was purified by column chromatography (silica gel, 85:15 hexane/EtOAc)

출처 및 근거

ORD 기록
ord-e0778a8402c9420b82131efcf9c02412
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465808B2

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