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

HRID 2165933
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인쇄 미리보기

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HRID 2165933 반응식
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10]Br)=[C:6]([CH2:14][CH2:15][CH3:16])[C:5]=1[OH:17])(=[O:3])[CH3:2].[SH:18][C:19]1[NH:20][C:21]2[CH:27]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:25]=[CH:24][C:22]=2[N:23]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[C:1]([C:4]1[CH:13]=[CH:12][C:7]([O:8][CH2:9][CH2:10][S:18][C:19]2[NH:20][C:21]3[CH:27]=[C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH:25]=[CH:24][C:22]=3[N:23]=2)=[C:6]([CH2:14][CH2:15][CH3:16])[C:5]=1[OH:17])(=[O:3])[CH3:2]
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참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 138819842-(4-Acetyl-3-hydroxy-2-propylphenoxy)ethyl bromideHCID 178468678HCID 178468678, 화합물

생성물 1

HCID 23042703Ethyl 2-[2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethylthio]benzimidazole-5-carboxylate수율 58.5%

시약·촉매·용매 1

HCID 6228
Dimethylformamide
용매

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온도
85 °C

실험 절차

A mixture of 2-(4-acetyl-3-hydroxy-2-propylphenoxy)ethyl bromide (2.71 g), ethyl 2 mercaptobenzimidazole-5-carboxylate (2.00 g) and anhydrous potassium carbonate (1.49 g) in N,N-dimethylformamide (30 ml) was stirred at 80-90 ° C. 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 dichloro-methane-ethyl acetate (10:1), to give ethyl 2-[2-(4-acetyl-3- hydroxy-2-propylphenoxy)ethylthio]benzimidazole-5-carboxylate (2.33 g, 58.5 %) as a yellow oil.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe resulting residue was purified by silica gel column chromatography
  6. washeluting with dichloro-methane-ethyl acetate (10:1)

출처 및 근거

ORD 기록
ord-75f3bd55358249e88a52045c386d9fa0
출처 데이터셋
uspto-grants-1990_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04942245

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