Water → 2-methyl-1-[4-(methylthio)butyl]-1H-imidazo[4,5-c]quinoline

HRID 497904

반응식

HRID 497904 반응식
[CH3:1][S-:2].[Na+].Cl[CH2:5][CH2:6][CH2:7][CH2:8][N:9]1[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=[C:10]1[CH3:22].O>CN(C)C=O>[CH3:22][C:10]1[N:9]([CH2:8][CH2:7][CH2:6][CH2:5][S:2][CH3:1])[C:21]2[C:20]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[N:14]=[CH:13][C:12]=2[N:11]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 223204561-(4-chlorobutyl)-2-methyl-1H-imidazo[4,5-c]quinoline

생성물 1

HCID 223204892-methyl-1-[4-(methylthio)butyl]-1H-imidazo[4,5-c]quinoline수율 95.9%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

Sodium thiomethoxide (2.02 g of 95%, 27.40 mmol) was added in a single portion to a solution of 1-(4-chlorobutyl)-2-methyl-1H-imidazo[4,5-c]quinoline (5.0 g, 18.26 mmol) in anhydrous N,N-dimethylformamide (91 mL). After 30 minutes the reaction mixture was poured with rapid stirring into water (500 mL). The resulting solution was extracted with chloroform (2×200 mL). The organic layers were combined, washed with saturated aqueous sodium bicarbonate (100 mL) then with brine (100 mL), dried over sodium sulfate, filtered and then concentrated under reduced pressure to provide 5.0 g 2-methyl-1-[4-(methylthio)butyl]-1H-imidazo[4,5-c]quinoline as a light yellow oil.

후처리

  1. additionAfter 30 minutes the reaction mixture was poured
  2. extractionThe resulting solution was extracted with chloroform (2×200 mL)
  3. washwashed with saturated aqueous sodium bicarbonate (100 mL)
  4. dry with materialwith brine (100 mL), dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c7f40a447a12452fb522564500af04a2
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949649B2

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