Hydrochloric Acid → 4-Nitro-3-[(phenylsulfonyl)methyl]-pyridine-N-oxide

HRID 1791147

반응식

HRID 1791147 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[CH2:12][S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14].[OH-].[K+].Cl>CS(C)=O.O>[N+:1]([C:4]1[CH:9]=[CH:8][N+:7]([O-:10])=[CH:6][C:5]=1[CH2:12][S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14])([O-:3])=[O:2]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 143004-Nitropyridine N-oxideHCID 14797Potassium HydroxideHCID 81625((Chloromethyl)sulphonyl)benzene

생성물 1

HCID 131990134-Nitro-3-[(phenylsulfonyl)methyl]-pyridine-N-oxide수율 41%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매2회HCID 962Water용매

실험 절차

Adapting the procedure of Makosza, et al, Liebigs Ann. Chem., 1984, 8–14, a stirred mixture of 4-nitro-pyridine-N-oxide (1.40 g, 10.0 mmol) and chloromethylphenylsulfone (1.92 g, 10.0 mmol) in DMSO (25 mL) in a cold water bath is treated with a solution of KOH (4.0 g, 71 mmol) in DMSO, stirred for 45 min, poured into 1.0 M hydrochloric acid and water and extracted with CH2Cl2. The aqueous phase is filtered and the filtercake is dried in vacuo to afford the title compound, 1.20 g (41% yield). The organic extracts are combined, dried over MgSO4 and concentrated in vacuo. The resultant wet solid is heated in boiling ethanol:water (4:1) and filtered. The filtrate is cooled, concentrated and filtered. This filtercake is dried in vacuo to afford an additional portion of the title compound, 0.967 g (74% total yield), mp 219–220° C., identified by mass spectral and HNMR analyses.

후처리

  1. extractionextracted with CH2Cl2
  2. filtrationThe aqueous phase is filtered
  3. customthe filtercake is dried in vacuo

출처 및 근거

ORD 기록
ord-2a0c127228ab49ed83a2eb76d54c03ad
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074792B2

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