Sodium Hydroxide → 5,6-dihydro-2-(quinolin-2-ylmethylthio)-4H-imidazo[4,5,1-ij]quinoline

HRID 256307노트

반응식

HRID 256307 반응식
[NH:1]1[C:11]2=[C:12]3[C:7](=[CH:8][CH:9]=[CH:10]2)[CH2:6][CH2:5][CH2:4][N:3]3[C:2]1=[S:13].[OH-].[Na+].Cl.Cl[CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1>C(O)C>[N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[CH2:18][S:13][C:2]1[N:3]2[C:12]3[C:7]([CH2:6][CH2:5][CH2:4]2)=[CH:8][CH:9]=[CH:10][C:11]=3[N:1]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 30838232-(Chloromethyl)quinoline hydrochlorideHCID 134578575,6-dihydro-2-mercapto[4H]imidazo [4,5,1-ij]quinoline

생성물 1

HCID 135032085,6-dihydro-2-(quinolin-2-ylmethylthio)-4H-imidazo[4,5,1-ij]quinoline수율 55.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 5,6-dihydro-4H-imidazo[4,5,1-ij]-quinoline-2(1H)-thione (2.02 g, 11.6 mmol) in ethanol (25 ml) and 1N-sodium hydroxide was treated with 2-(chloromethyl)quinoline hydrochloride (2.48 g, 11.6 mmol) heated to reflux, cooled to room temperature, and the ethanol removed by evaporation in vacuo. The aqueous mixture was filtered and the precipitate washed with water (5×50 ml), dried in vacuo, and recrystallised from cyclohexane - EtOAc to give 5,6-dihydro-2-(quinolin-2-ylmethylthio)-4H-imidazo[4,5,1-ij]quinoline (2.13 g, 55%) as yellow crystals mp 125°-126° C. (Found: C, 72.8; H, 5.3; N,12.4 C20H17N3S requires C, 72.5; H, 5.2; N, 12.7%).

후처리

  1. temperatureheated
  2. temperatureto reflux
  3. customthe ethanol removed by evaporation in vacuo
  4. filtrationThe aqueous mixture was filtered
  5. washthe precipitate washed with water (5×50 ml)
  6. customdried in vacuo
  7. customrecrystallised from cyclohexane - EtOAc

출처 및 근거

ORD 기록
ord-d6f32f06ec2046bc8777a1bb1141b6b5
출처 데이터셋
uspto-grants-1987_10
특허 번호
US04703044

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