2,3-Dimethylbenzoic acid → HCID 21890373, compound

HRID 721794Notes

Reaction equation

HRID 721794 reaction equation
S(Cl)(Cl)=O.CC1C(C)=CC=CC=1C(O)=O.CC1C(C)=CC=CC=1C(Cl)=O.[CH3:27][C:28]1[C:33]([CH3:34])=[CH:32][CH:31]=[CH:30][C:29]=1[C:35]([N:37]=[C:38]=[S:39])=[O:36].[Cl:40][C:41]1[CH:42]=[C:43]([CH:45]=[CH:46][C:47]=1[O:48][C:49]1[C:58]2[C:53](=[CH:54][C:55]([O:61][CH3:62])=[C:56]([O:59][CH3:60])[CH:57]=2)[N:52]=[CH:51][CH:50]=1)[NH2:44]>C(O)C.C1(C)C=CC=CC=1>[Cl:40][C:41]1[CH:42]=[C:43]([NH:44][C:38]([NH:37][C:35](=[O:36])[C:29]2[CH:30]=[CH:31][CH:32]=[C:33]([CH3:34])[C:28]=2[CH3:27])=[S:39])[CH:45]=[CH:46][C:47]=1[O:48][C:49]1[C:58]2[C:53](=[CH:54][C:55]([O:61][CH3:62])=[C:56]([O:59][CH3:60])[CH:57]=2)[N:52]=[CH:51][CH:50]=1

Participants

8

Reactant 5

HCID 117822,3-Dimethylbenzoic acidHCID 24386Thionyl ChlorideHCID 28008992,3-Dimethylbenzoyl chlorideHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 21890261HCID 21890261, compound

Product 1

HCID 21890373HCID 21890373, compoundYield 96%

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 2,3-dimethylbenzoic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 2,3-dimethyl-1-benzenecarbonyl isothiocyanate was prepared using the resultant 2,3-dimethyl-1-benzenecarbonyl chloride as a starting compound according to the description of the literature. 2,3-Dimethyl-1-benzenecarbonyl 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 (76 mg, yield 96%).

Workup

  1. customThe solvent was removed by distillation, and 2,3-dimethyl-1-benzenecarbonyl 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-f16bd56acde54f34863d6da6cd8b0c2d
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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