Thionyl Chloride → N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-[3-(2-methylphenyl)propanoyl]thiourea

HRID 721907

반응식

HRID 721907 반응식
S(Cl)(Cl)=O.CC1C=CC=CC=1CCC(O)=O.CC1C=CC=CC=1CCC(Cl)=O.[CH3:29][O:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][C:40]=1[O:41][CH3:42])[N:37]=[CH:36][N:35]=[C:34]2[O:43][C:44]1[CH:50]=[CH:49][C:47]([NH2:48])=[CH:46][CH:45]=1.[CH3:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=1[CH2:58][CH2:59][C:60]([N:62]=[C:63]=[S:64])=[O:61]>C1(C)C=CC=CC=1.C(O)C>[CH3:29][O:30][C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][C:40]=1[O:41][CH3:42])[N:37]=[CH:36][N:35]=[C:34]2[O:43][C:44]1[CH:50]=[CH:49][C:47]([NH:48][C:63]([NH:62][C:60](=[O:61])[CH2:59][CH2:58][C:53]2[CH:54]=[CH:55][CH:56]=[CH:57][C:52]=2[CH3:51])=[S:64])=[CH:46][CH:45]=1

참가 물질

8

반응물 5

HCID 24386Thionyl ChlorideHCID 309383-(2-Methylphenyl)propionic acidHCID 116163634-(6,7-Dimethoxyquinazolin-4-yloxy)anilineHCID 130292013-(2-Methylphenyl)propanoyl chlorideHCID 218907013-(2-Methylphenyl)propanoyl isothiocyanate

생성물 1

HCID 21889957N-{4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]phenyl}-N'-[3-(2-methylphenyl)propanoyl]thiourea수율 57%

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-(2-methylphenyl)propanoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 3-(2-methylphenyl)propanoyl isothiocyanate was prepared using the resultant 3-(2-methylphenyl)propanoyl chloride as a starting compound according to the description of the literature. 4-[(6,7-Dimethoxy-4-quinazolinyl)oxy]aniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 3-(2-methylphenyl)propanoyl 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 (48 mg, yield 57%).

후처리

  1. customThe solvent was removed by distillation, and 3-(2-methylphenyl)propanoyl 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-35ea3f3fc5f64d2f83ebe787358ae9e2
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07135466B2

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