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p-Toluenesulfonic acid → 6-chloro-N-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-N-phenylpyridine-3-sulfonamide

HRID 45263
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HRID 45263 반응식
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]([CH2:18][CH:19]([OH:22])[CH2:20][OH:21])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.CO[C:25](OC)([CH3:27])[CH3:26].CC1C=CC(S(O)(=O)=O)=CC=1>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]([CH2:18][CH:19]2[CH2:20][O:21][C:25]([CH3:27])([CH3:26])[O:22]2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1
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참가 물질

6

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 64952,2-DimethoxypropaneHCID 866597566-chloro-N-(2,3-dihydroxypropyl)-N-phenylpyridine-3-sulfonamide

생성물 1

HCID 866597576-chloro-N-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-N-phenylpyridine-3-sulfonamide수율 73%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매
HCID 8857
Ethyl Acetate
용매

실험 절차

A mixture of 0.67 g (1.96 mmol) of 6-chloro-N-(2,3-dihydroxypropyl)-N-phenylpyridine-3-sulfonamide, 0.53 mL (4.3 mmol) of 2,2-dimethoxypropane and 37 mg of pTsOH in 4 mL of DMF is stirred for 3 hours at room temperature. The medium is taken up in 100 mL of EtOAc, washed with 50 mL of saturated NaHCO3 solution and 50 mL of water and then dried over Na2SO4, filtered and concentrated under reduced pressure. 0.54 g 6-chloro-N-[(2,2-dimethyl-1,3-dioxolan-4-yl)methyl]-N-phenylpyridine-3-sulfonamide is obtained in the form of a brown solid, which is used without further purification in the following step.

후처리

  1. washwashed with 50 mL of saturated NaHCO3 solution and 50 mL of water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-948e494dd4404503a7705e9713854a8a
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08541455B2

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