Sodium Hydroxide → 5-[(4,5-Diphenyl-1H-imidazol-2-YL)sulfanyl]pentanoic acid

HRID 1109047노트

반응식

HRID 1109047 반응식
C([O:3][C:4](=[O:27])[CH2:5][CH2:6][CH2:7][CH2:8][S:9][C:10]1[NH:11][C:12]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:14]=1)C.[OH-].[Na+]>C(O)C.O>[C:21]1([C:12]2[N:11]=[C:10]([S:9][CH2:8][CH2:7][CH2:6][CH2:5][C:4]([OH:27])=[O:3])[NH:14][C:13]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

참가 물질

5

반응물 2

HCID 14798Sodium HydroxideHCID 542015795-(4,5-diphenyl-1H-imidazol-2-ylthio)pentanoic acid ethyl ester

생성물 1

HCID 189587125-[(4,5-Diphenyl-1H-imidazol-2-YL)sulfanyl]pentanoic acid수율 55%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

Part B. To a solution of 5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentanoic acid ethyl ester (7.6 g, 0.02 mol) in ethanol (200 mL), was added dropwise a solution of sodium hydroxide (7.6 g) in water (200 mL), and the reaction mixture was stirred at reflux under nitrogen for 3 hours. The reaction mixture was concentrated to half the original volume and then extracted with ether. The ether extracts were discarded. The reaction mixture was acidified to pH 1 with 1N hydrochloric acid and extracted with ether, and the combined organic extracts were dried over magnesium sulfate and concentrated under vacuum. The resulting solid was recrystallized from acetonitrile and triturated with hexane to give 5-(4.5-diphenyl-1H-imidazol-2-ylthio) pentanoic acid (3.88 g, 0.011 mol) as a white solid, mp 190°-195°. 1H NMR (DMSO-d6) δ 12.6(s,1H) , 7.6-7.1(m,10H), 3.3-3.1 (m,2H), 2.3-2.1 (m,3H), 1.8-1.6 (m,4H).

후처리

  1. temperatureat reflux under nitrogen for 3 hours
  2. concentrationThe reaction mixture was concentrated to half the original volume
  3. extractionextracted with ether
  4. extractionextracted with ether
  5. dry with materialthe combined organic extracts were dried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe resulting solid was recrystallized from acetonitrile
  8. customtriturated with hexane

출처 및 근거

ORD 기록
ord-c0c16de98bb84a82b2ec28875009eca4
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05318984

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