Thionyl Chloride → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-fluorophenyl}-N'-[(2,5-dimethyl-3-furyl)carbonyl]thiourea

HRID 721815

反応式

HRID 721815 の反応式
S(Cl)(Cl)=O.CC1OC(C)=CC=1C(O)=O.CC1OC(C)=CC=1C(Cl)=O.[CH3:25][C:26]1[O:27][C:28]([CH3:36])=[CH:29][C:30]=1[C:31]([N:33]=[C:34]=[S:35])=[O:32].[CH3:37][O:38][C:39]1[CH:40]=[C:41]2[C:46](=[CH:47][C:48]=1[O:49][CH3:50])[N:45]=[CH:44][CH:43]=[C:42]2[O:51][C:52]1[CH:58]=[CH:57][C:55]([NH2:56])=[CH:54][C:53]=1[F:59]>C(O)C.C1(C)C=CC=CC=1>[CH3:37][O:38][C:39]1[CH:40]=[C:41]2[C:46](=[CH:47][C:48]=1[O:49][CH3:50])[N:45]=[CH:44][CH:43]=[C:42]2[O:51][C:52]1[CH:58]=[CH:57][C:55]([NH:56][C:34]([NH:33][C:31]([C:30]2[CH:29]=[C:28]([CH3:36])[O:27][C:26]=2[CH3:25])=[O:32])=[S:35])=[CH:54][C:53]=1[F:59]

参加物

8

反応物 5

HCID 24386Thionyl ChlorideHCID 694652,5-Dimethyl-3-furoic acidHCID 27348042,5-Dimethyl-3-furoyl ChlorideHCID 114269974-((6,7-Dimethoxyquinolin-4-yl)oxy)-3-fluorobenzenamineHCID 150825562,5-Dimethyl-3-furancarbonyl isothiocyanate

生成物 1

HCID 21890065N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-fluorophenyl}-N'-[(2,5-dimethyl-3-furyl)carbonyl]thiourea収率 64%

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 2,5-dimethyl-3-furoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 2,5-dimethyl-3-furancarbonyl isothiocyanate was prepared using the resultant 2,5-dimethyl-3-furancarbonyl chloride as a starting compound according to the description of the literature. 2,5-Dimethyl-3-furancarbonyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-fluoroaniline (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 (51 mg, yield 64%).

後処理

  1. customThe solvent was removed by distillation, and 2,5-dimethyl-3-furancarbonyl 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-717fe8fb91574f4194f59300401eeca6
出典データセット
uspto-grants-2006_11
特許番号
US07135466B2

関連ノート

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