2-Thiopheneacetic acid → N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-[2-(2-thienyl)acetyl]thiourea

HRID 721946Notes

Reaction equation

S(Cl)(Cl)=O.S1C=CC=C1CC(O)=O.S1C=CC=C1CC(Cl)=O.[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][C:34]=1[O:35][CH3:36])[N:31]=[CH:30][CH:29]=[C:28]2[O:37][C:38]1[CH:44]=[CH:43][C:41]([NH2:42])=[CH:40][CH:39]=1.[S:45]1[CH:49]=[CH:48][CH:47]=[C:46]1[CH2:50][C:51]([N:53]=[C:54]=[S:55])=[O:52]>C1(C)C=CC=CC=1.C(O)C>[CH3:23][O:24][C:25]1[CH:26]=[C:27]2[C:32](=[CH:33][C:34]=1[O:35][CH3:36])[N:31]=[CH:30][CH:29]=[C:28]2[O:37][C:38]1[CH:44]=[CH:43][C:41]([NH:42][C:54]([NH:53][C:51](=[O:52])[CH2:50][C:46]2[S:45][CH:49]=[CH:48][CH:47]=2)=[S:55])=[CH:40][CH:39]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Toluene (20 ml) and thionyl chloride (1 ml) were added to commercially available 2-(2-thienyl)acetic acid (40 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 2-(2-thienyl)ethanoyl isothiocyanate was prepared using the resultant 2-(2-thienyl)ethanoyl 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 2-(2-thienyl)ethanoyl 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 54%).

Workup

customThe solvent was removed by distillation, and 2-(2-thienyl)ethanoyl isothiocyanate
customwas prepared
concentrationThe reaction solution was concentrated
customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-3c0cdade7d10477cb00c9c5a3eb162e4
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135466B2

Reaction notes

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