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

HRID 721841

反応式

HRID 721841 の反応式
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].[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][C:42]=1[O:43][CH3:44])[N:39]=[CH:38][CH:37]=[C:36]2[O:45][C:46]1[CH:52]=[CH:51][C:49]([NH2:50])=[CH:48][CH:47]=1>C(O)C.C1(C)C=CC=CC=1>[CH3:31][O:32][C:33]1[CH:34]=[C:35]2[C:40](=[CH:41][C:42]=1[O:43][CH3:44])[N:39]=[CH:38][CH:37]=[C:36]2[O:45][C:46]1[CH:47]=[CH:48][C:49]([NH:50][C:29]([NH:28][C:26](=[O:27])[CH2:25][CH2:24][O:23][CH2:21][CH3:22])=[S:30])=[CH:51][CH:52]=1

参加物

8

反応物 5

HCID 24386Thionyl ChlorideHCID 613513-Ethoxypropionic acidHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 124253413-Ethoxypropanoyl chlorideHCID 218904773-Ethoxypropanoyl isothiocyanate

生成物 1

HCID 21890737N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-(3-ethoxypropanoyl)thiourea収率 72%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒2 回HCID 1140Toluene溶媒2 回

反応条件

温度
100 °C

実験手順

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. 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 (55 mg, yield 72%).

後処理

  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

出典と根拠

ORDレコード
ord-2c1efa9ef32b4a85bba513680ef3c64b
出典データセット
uspto-grants-2006_11
特許番号
US07135466B2

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