Thionyl Chloride → HCID 21889926, compound

HRID 721814Notes

Reaction equation

HRID 721814 reaction equation
S(Cl)(Cl)=O.CC1C=CSC=1C(O)=O.CC1C=CSC=1C(Cl)=O.[CH3:23][C:24]1[CH:28]=[CH:27][S:26][C:25]=1[C:29]([N:31]=[C:32]=[S:33])=[O:30].[CH3:34][O:35][C:36]1[CH:37]=[C:38]2[C:43](=[CH:44][C:45]=1[O:46][CH3:47])[N:42]=[CH:41][CH:40]=[C:39]2[O:48][C:49]1[CH:55]=[CH:54][C:52]([NH2:53])=[C:51]([F:56])[CH:50]=1>C(O)C.C1(C)C=CC=CC=1>[CH3:34][O:35][C:36]1[CH:37]=[C:38]2[C:43](=[CH:44][C:45]=1[O:46][CH3:47])[N:42]=[CH:41][CH:40]=[C:39]2[O:48][C:49]1[CH:55]=[CH:54][C:52]([NH:53][C:32]([NH:31][C:29]([C:25]2[S:26][CH:27]=[CH:28][C:24]=2[CH3:23])=[O:30])=[S:33])=[C:51]([F:56])[CH:50]=1

Participants

8

Reactant 5

HCID 24386Thionyl ChlorideHCID 902693-Methyl-2-thenoic acidHCID 27376053-Methyl-2-thenoyl ChlorideHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroanilineHCID 21890380HCID 21890380, compound

Product 1

HCID 21889926HCID 21889926, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent2×

Conditions

Temperature
100 °C

Procedure

Toluene (20 ml) and thionyl chloride (1 ml) were added to commercially available 3-methyl-2-thiophenecarboxylic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 3-methyl-2-thiophenecarbonyl isothiocyanate was prepared using the resultant 3-methyl-2-thiophenecarbonyl chloride as a starting compound according to the description of the literature. 3-Methyl-2-thiophenecarbonyl isothiocyanate was dissolved in ethanol (1 ml) to prepare a solution. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-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 (42 mg, yield 53%).

Workup

  1. customThe solvent was removed by distillation, and 3-methyl-2-thiophenecarbonyl 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

Sources & evidence

ORD record
ord-d4b873a5cceb4ca990db2723bf5c5e30
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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