Thionyl Chloride → N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(3-ethoxypropanoyl)thiourea

HRID 721847

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HRID 721847 반응식
S(Cl)(Cl)=O.C(OCCC(O)=O)C.C(OCCC(Cl)=O)C.[CH2:21]([O:23][CH2:24][CH2:25][C:26]([N:28]=[C:29]=[S:30])=[O:27])[CH3:22].[Cl:31][C:32]1[CH:33]=[C:34]([CH:36]=[CH:37][C:38]=1[O:39][C:40]1[C:49]2[C:44](=[CH:45][C:46]([O:52][CH3:53])=[C:47]([O:50][CH3:51])[CH:48]=2)[N:43]=[CH:42][CH:41]=1)[NH2:35]>C(O)C.C1(C)C=CC=CC=1>[Cl:31][C:32]1[CH:33]=[C:34]([NH:35][C:29]([NH:28][C:26](=[O:27])[CH2:25][CH2:24][O:23][CH2:21][CH3:22])=[S:30])[CH:36]=[CH:37][C:38]=1[O:39][C:40]1[C:49]2[C:44](=[CH:45][C:46]([O:52][CH3:53])=[C:47]([O:50][CH3:51])[CH:48]=2)[N:43]=[CH:42][CH:41]=1

참가 물질

8

반응물 5

HCID 24386Thionyl ChlorideHCID 613513-Ethoxypropionic acidHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 124253413-Ethoxypropanoyl chlorideHCID 218904773-Ethoxypropanoyl isothiocyanate

생성물 1

HCID 21891137N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(3-ethoxypropanoyl)thiourea수율 62%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 1140Toluene용매2회

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온도
100 °C

실험 절차

Toluene (20 ml) and thionyl chloride (1 ml) were added to commercially available 3-ethoxypropanoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 3-ethoxypropanoyl isothiocyanate was prepared using the resultant 3-ethoxypropanoyl chloride as a starting compound according to the description of the literature. 3-Ethoxypropanoyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (50 mg), toluene (5 ml), and ethanol (1 ml) were added to the solution, and the mixture was stirred at room temperature for 2 hr. The reaction solution was concentrated, and the residue was purified by chromatography on silica gel using chloroform/acetone for development to give the title compound (46 mg, yield 62%).

후처리

  1. customThe solvent was removed by distillation, and 3-ethoxypropanoyl isothiocyanate
  2. customwas prepared
  3. customto prepare a solution
  4. concentrationThe reaction solution was concentrated
  5. customthe residue was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-53d49e3c28ed4b73a7baef6aa2cc3bea
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135466B2

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