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

HRID 721897노트

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HRID 721897 반응식
S(Cl)(Cl)=O.C1(C2C=CC(C(O)=O)=CC=2)CCCCC1.C1(C2C=CC(C(Cl)=O)=CC=2)CCCCC1.[CH3:35][O:36][C:37]1[CH:38]=[C:39]2[C:44](=[CH:45][C:46]=1[O:47][CH3:48])[N:43]=[CH:42][CH:41]=[C:40]2[O:49][C:50]1[CH:56]=[CH:55][C:53]([NH2:54])=[CH:52][CH:51]=1.[CH:57]1([C:63]2[CH:68]=[CH:67][C:66]([C:69]([N:71]=[C:72]=[S:73])=[O:70])=[CH:65][CH:64]=2)[CH2:62][CH2:61][CH2:60][CH2:59][CH2:58]1>C1(C)C=CC=CC=1.C(O)C>[CH:57]1([C:63]2[CH:64]=[CH:65][C:66]([C:69]([NH:71][C:72]([NH:54][C:53]3[CH:55]=[CH:56][C:50]([O:49][C:40]4[C:39]5[C:44](=[CH:45][C:46]([O:47][CH3:48])=[C:37]([O:36][CH3:35])[CH:38]=5)[N:43]=[CH:42][CH:41]=4)=[CH:51][CH:52]=3)=[S:73])=[O:70])=[CH:67][CH:68]=2)[CH2:58][CH2:59][CH2:60][CH2:61][CH2:62]1

참가 물질

8

반응물 5

HCID 24386Thionyl ChlorideHCID 883374-Cyclohexylbenzoic acidHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 218904044-Cyclohexyl-1-benzenecarbonyl isothiocyanateHCID 218908474-Cyclohexylbenzoyl chloride

생성물 1

HCID 21890920N-(4-Cyclohexylbenzoyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thiourea수율 48%

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 4-cyclohexylbenzoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 4-cyclohexyl-1-benzenecarbonyl isothiocyanate was prepared using the resultant 4-cyclohexyl-1-benzenecarbonyl chloride as a starting compound according to the description of the literature. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 4-cyclohexyl-1-benzenecarbonyl isothiocyanate in ethanol (1 ml) was then 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 (44 mg, yield 48%).

후처리

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

출처 및 근거

ORD 기록
ord-b362681e32e34c7aa70d468729c58973
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135466B2

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