N-bromobutanimide → N-[5-bromo-6-(2-hydroxyethoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide

HRID 2309

반응식

HRID 2309 반응식
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[C:19]([O:21][CH2:22][CH2:23][OH:24])[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[Br:25]N1C(=O)CCC1=O.S([O-])(O)=O.[Na+]>CN(C)C=O>[Br:25][C:20]1[C:15]([NH:14][S:11]([C:8]2[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[CH:6][CH:7]=2)(=[O:12])=[O:13])=[N:16][CH:17]=[N:18][C:19]=1[O:21][CH2:22][CH2:23][OH:24]

참가 물질

5

반응물 3

HCID 67184N-bromobutanimideHCID 117831024-tert-butyl-N-[6-(2-hydroxyethoxy)pyrimidin-4-yl)benzenesulfonamideHCID 23665763Sodium Bisulfite

생성물 1

HCID 11026374N-[5-bromo-6-(2-hydroxyethoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide수율 65.7%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 4-tert-butyl-N-[6-(2-hydroxyethoxy)pyrimidin-4-yl)benzenesulfonamide (210 mg) in dimethylformamide (4 ml) is added N-bromosuccinimide (116 mg), and the mixture is stirred at room temperature for one hour. The mixture is treated with aqueous sodium hydrogen sulfite solution, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1), and recrystallized from hexane/ethyl acetate to give N-[5-bromo-6-(2-hydroxyethoxy)pyrimidin-4-yl]-4-tert-butylbenzenesulfonamide (169 mg).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer is washed
  3. customdried
  4. customevaporated
  5. customto remove the solvent
  6. customThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=40:1)
  7. customrecrystallized from hexane/ethyl acetate

출처 및 근거

ORD 기록
ord-da9e15d8493a44cfbbae58022cf084ac
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05728706

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