Sodium Hydroxide → 5,6-Dihydro-8-methoxy-2-[(6-phenylpyridin-2-yl)-methylthio]-4H-imidazo[4,5,1-ij]quinoline

HRID 256306노트

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HRID 256306 반응식
Cl.Cl[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:5]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25]3=[C:26]([NH:28][C:29](=[S:30])[N:24]3[CH2:23][CH2:22][CH2:21]2)[CH:27]=1.[OH-].[Na+]>C(O)C>[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25]3=[C:26]([N:28]=[C:29]([S:30][CH2:3][C:4]4[CH:9]=[CH:8][CH:7]=[C:6]([C:10]5[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=5)[N:5]=4)[N:24]3[CH2:23][CH2:22][CH2:21]2)[CH:27]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 135032135,6-dihydro-8-methoxy-2-mercapto-4H-imidazo[4,5,1-ij]quinolineHCID 199011562-Chloromethyl-6-phenylpyridine hydrochloride

생성물 1

HCID 135032075,6-Dihydro-8-methoxy-2-[(6-phenylpyridin-2-yl)-methylthio]-4H-imidazo[4,5,1-ij]quinoline

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

2-Chloromethyl-6-phenylpyridine hydrochloride 1.942 g, 8.1 mmol) was added to a solution of 5,6-dihydro-8-methoxy-4H-imidazo[4,5,1-ij]quinoline-2[1H]-thione (1.78 g, 8.1 mmol) in ethanol (16 ml) and 1N-sodium hydroxide (16.2 ml). The mixture was heated under reflux for 15 seconds and cooled to room temperature. The ethanol was removed by evaporation in vacuo and the aqueous mixture extracted with dichloromethane (2×150 ml). The extracts were dried (MgSO4) and evaporated in vacuo to give a brown solid which was recrystallised from MeOH to give the title compound as the quarter hydrate (2.77 g, 88%), mp 134°-135° C. (Found: C, 70.5; H, 5.8; N, 10.4; C23H21N3OS1/4H2O requires C, 70.5; H, 5.5; N, 10.7%).

후처리

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 15 seconds
  3. customThe ethanol was removed by evaporation in vacuo
  4. extractionthe aqueous mixture extracted with dichloromethane (2×150 ml)
  5. dry with materialThe extracts were dried (MgSO4)
  6. customevaporated in vacuo
  7. customto give a brown solid which
  8. customwas recrystallised from MeOH

출처 및 근거

ORD 기록
ord-31386b8b23594ff7ae6794e70eea2862
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04703044

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