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Water → 5-(4-Methanesulfonyl-phenoxy)-3-(2-methoxy-ethoxy)-2-nitro-pyridine

HRID 1966253
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HRID 1966253 반응식
Cl[C:2]1[CH:3]=[C:4]([O:11][CH2:12][CH2:13][O:14][CH3:15])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=1.[CH3:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1)(=[O:19])=[O:18].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:16][S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][C:2]2[CH:3]=[C:4]([O:11][CH2:12][CH2:13][O:14][CH3:15])[C:5]([N+:8]([O-:10])=[O:9])=[N:6][CH:7]=2)=[CH:22][CH:21]=1)(=[O:18])=[O:19]
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참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 1233504-(Methylsulfonyl)phenolHCID 674861005-Chloro-3-(2-methoxy-ethoxy)-2-nitro-pyridine

생성물 1

HCID 674867165-(4-Methanesulfonyl-phenoxy)-3-(2-methoxy-ethoxy)-2-nitro-pyridine수율 15%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
120 °C

실험 절차

5-Chloro-3-(2-methoxy-ethoxy)-2-nitro-pyridine (2.6 mmol) is dissolved in DMF (12 ml), 4-(methylsulfonyl)phenol (3 eq.) and K2CO3 (4 eq.) is added. The reaction is heated to 120° C. in the microwave for 45 min. The reaction solution is pored into water and extracted with Methyltert.-butyl ether. The combined organic layers are washed with brine, dried over MgSO4 and the solvent is removed in vacuo. 5-(4-Methanesulfonyl-phenoxy)-3-(2-methoxy-ethoxy)-2-nitro-pyridine is obtained after column chromatography (heptane/ethyl acetate) as yellow oil in a yield of 15%. HPLC (method C): 1.65 min; LC-MS (method A): 1.534 min, 369.1 (MH+).

후처리

  1. extractionextracted with Methyltert.-butyl ether
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent is removed in vacuo

출처 및 근거

ORD 기록
ord-cb3296d5b472423c92755a91f8274684
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08420642B2

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