2,4-Dimethylbenzoic acid → N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(2,4-dimethylbenzoyl)thiourea

HRID 721792

반응식

HRID 721792 반응식
S(Cl)(Cl)=O.CC1C=C(C)C=CC=1C(O)=O.CC1C=C(C)C=CC=1C(Cl)=O.[CH3:27][C:28]1[CH:33]=[C:32]([CH3:34])[CH:31]=[CH:30][C:29]=1[C:35]([N:37]=[C:38]=[S:39])=[O:36].[Cl:40][C:41]1[CH:42]=[C:43]([CH:45]=[CH:46][C:47]=1[O:48][C:49]1[C:58]2[C:53](=[CH:54][C:55]([O:61][CH3:62])=[C:56]([O:59][CH3:60])[CH:57]=2)[N:52]=[CH:51][CH:50]=1)[NH2:44]>C(O)C.C1(C)C=CC=CC=1>[Cl:40][C:41]1[CH:42]=[C:43]([NH:44][C:38]([NH:37][C:35](=[O:36])[C:29]2[CH:30]=[CH:31][C:32]([CH3:34])=[CH:33][C:28]=2[CH3:27])=[S:39])[CH:45]=[CH:46][C:47]=1[O:48][C:49]1[C:58]2[C:53](=[CH:54][C:55]([O:61][CH3:62])=[C:56]([O:59][CH3:60])[CH:57]=2)[N:52]=[CH:51][CH:50]=1

참가 물질

8

반응물 5

HCID 118972,4-Dimethylbenzoic acidHCID 24386Thionyl ChlorideHCID 1408672,4-Dimethylbenzoyl chlorideHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 167781212,4-Dimethyl-1-benzenecarbonyl isothiocyanate

생성물 1

HCID 21890757N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(2,4-dimethylbenzoyl)thiourea수율 97%

시약·촉매·용매 2

HCID 702Ethanol용매2회HCID 1140Toluene용매2회

반응 조건

온도
100 °C

실험 절차

Toluene (20 ml) and thionyl chloride (1 ml) were added to commercially available 2,4-dimethylbenzoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 2,4-dimethyl-1-benzenecarbonyl isothiocyanate was prepared using the resultant 2,4-dimethyl-1-benzenecarbonyl chloride as a starting compound according to the description of the literature. 2,4-Dimethyl-1-benzenecarbonyl 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 (75 mg, yield 97%).

후처리

  1. customThe solvent was removed by distillation, and 2,4-dimethyl-1-benzenecarbonyl 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-85e1fbc15754446e9f612df0588f832b
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135466B2

연결된 노트

불러오는 중…