2-Methylhexanoic Acid → N-{3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}-N'-(2-methylhexanoyl)thiourea

HRID 721852

Reaction equation

S(Cl)(Cl)=O.CC(CCCC)C(O)=O.CC(CCCC)C(Cl)=O.[CH3:23][CH:24]([CH2:30][CH2:31][CH2:32][CH3:33])[C:25]([N:27]=[C:28]=[S:29])=[O:26].[Cl:34][C:35]1[CH:36]=[C:37]([CH:39]=[CH:40][C:41]=1[O:42][C:43]1[C:52]2[C:47](=[CH:48][C:49]([O:55][CH3:56])=[C:50]([O:53][CH3:54])[CH:51]=2)[N:46]=[CH:45][CH:44]=1)[NH2:38]>C(O)C.C1(C)C=CC=CC=1>[Cl:34][C:35]1[CH:36]=[C:37]([NH:38][C:28]([NH:27][C:25](=[O:26])[CH:24]([CH3:23])[CH2:30][CH2:31][CH2:32][CH3:33])=[S:29])[CH:39]=[CH:40][C:41]=1[O:42][C:43]1[C:52]2[C:47](=[CH:48][C:49]([O:55][CH3:56])=[C:50]([O:53][CH3:54])[CH:51]=2)[N:46]=[CH:45][CH:44]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Toluene (20 ml) and thionyl chloride (1 ml) were added to commercially available 2-methylhexanoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 2-methylhexanoyl isothiocyanate was prepared using the resultant 2-methylhexanoyl chloride as a starting compound according to the description of the literature. 2-Methylhexanoyl 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 (44 mg, yield 58%).

Workup

customThe solvent was removed by distillation, and 2-methylhexanoyl isothiocyanate
customwas prepared
customto prepare a solution
concentrationThe reaction solution was concentrated
customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record: ord-0fb699b800a14b92bce820149a6026a2
Source dataset: uspto-grants-2006_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07135466B2

Linked notes

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