Hydrochloric Acid → Ethyl 2-[4-(4-acetyl-3-hydroxy-2-propylphenylthio)butylthio]benzimidazole-5-carboxylate

HRID 2165940노트

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HRID 2165940 반응식
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][C:5]=2[N:6]=1.C(=O)([O-])[O-].[K+].[K+].[C:22]([C:25]1[CH:30]=[CH:29][C:28]([S:31][CH2:32][CH2:33][CH2:34][CH2:35]Br)=[C:27]([CH2:37][CH2:38][CH3:39])[C:26]=1[OH:40])(=[O:24])[CH3:23].Cl>CN(C)C=O>[C:22]([C:25]1[CH:30]=[CH:29][C:28]([S:31][CH2:32][CH2:33][CH2:34][CH2:35][S:1][C:2]2[NH:3][C:4]3[CH:10]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:8]=[CH:7][C:5]=3[N:6]=2)=[C:27]([CH2:37][CH2:38][CH3:39])[C:26]=1[OH:40])(=[O:24])[CH3:23]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 157123844-(4-Acetyl-3-hydroxy-2-propylphenylthio)butylbromideHCID 178468678HCID 178468678, 화합물

생성물 1

HCID 23042700Ethyl 2-[4-(4-acetyl-3-hydroxy-2-propylphenylthio)butylthio]benzimidazole-5-carboxylate수율 89.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
65 °C

실험 절차

A mixture of ethyl 2-mercaptobenzimidazole-5-carboxylate (1.29 g), anhydrous potassium carbonate (960 mg) in N,N-dimethylformamide (20 ml) was stirred at 60-70 ° C. for 30 minutes. To this mixture was added a solution of 4-(4-acetyl-3-hydroxy-2-propylphenylthio)butylbromide (2.00 g) in N,N-dimethylformamide (10 ml) dropwise during 10 minutes and stirred at the same temperature for 30 minutes. The reaction mixture was poured into ice-water, made acidic with concentrated hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and evaporated. The resulting residue was purified by silica gel column chromatography, eluting with dichloromethane-ethyl acetate 10:1), to give the title compound (2.53 g, 89.8%) as pale yellow oil.

후처리

  1. stirringstirred at the same temperature for 30 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated
  6. customThe resulting residue was purified by silica gel column chromatography
  7. washeluting with dichloromethane-ethyl acetate 10:1),

출처 및 근거

ORD 기록
ord-31a3b21fb6d446279bfa009b45d6fddc
출처 데이터셋
uspto-grants-1990_07
특허 번호
US04942245

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