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Water → ethyl 5-[4,5-bis(4-methoxyphenyl)-1H-imidazole-2-ylthio]pentanoate

HRID 1033246
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HRID 1033246 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([SH:22])[NH:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.Br[CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29].C(=O)([O-])[O-].[K+].[K+].O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]=[C:11]([S:22][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[NH:10][C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:15][CH:16]=1
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참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 84580Ethyl 5-bromovalerateHCID 178489021HCID 178489021, 화합물

생성물 1

HCID 10094797ethyl 5-[4,5-bis(4-methoxyphenyl)-1H-imidazole-2-ylthio]pentanoate수율 103.2%

시약·촉매·용매 2

HCID 67553
Tetrabutylammonium Iodide
촉매
HCID 8028Tetrahydrofuran용매

실험 절차

Part A. A suspension of 4,5-bis(4-methoxyphenyl)-2-mercapto-1H-imidazole (10.4 g, 33.2 mmol), ethyl 5-bromovalerate (5.00 mL, 31.6 mmol), potassium carbonate (5.50 g, 39.8 mmol), and tetra-n-butylammonium iodide (2 g) in tetrahydrofuran (100 mL) was heated to reflux for 20 hours. The mixture was cooled, and poured into water (400 mL). This was extracted with methylene chloride (2 ×400 mL), and the extracts were combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The residual oil was purified by elution through a short plug of silica gel with ethyl acetate, and evaporation afforded ethyl 5-[4,5-bis(4-methoxyphenyl)-1H-imidazole-2-ylthio]pentanoate (14.4 g, 32.6 mmol, 98%) as a waxy, low-melting solid.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 20 hours
  3. temperatureThe mixture was cooled
  4. extractionThis was extracted with methylene chloride (2 ×400 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residual oil was purified by elution through a short plug of silica gel with ethyl acetate, and evaporation

출처 및 근거

ORD 기록
ord-298db64730b94ab5ab0f0411a5bc672e
출처 데이터셋
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05310748

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