Thionyl Chloride → HCID 21890294, compound

HRID 721919Notes

Reaction equation

HRID 721919 reaction equation
S(Cl)(Cl)=O.CC1SC(C(O)=O)=CC=1.CC1SC(C(Cl)=O)=CC=1.[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.[CH3:45][C:46]1[S:50][C:49]([C:51]([N:53]=[C:54]=[S:55])=[O:52])=[CH:48][CH:47]=1>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]([C:49]2[S:50][C:46]([CH3:45])=[CH:47][CH:48]=2)=[O:52])=[S:55])=[CH:40][CH:39]=1

Participants

8

Reactant 5

HCID 24386Thionyl ChlorideHCID 747135-Methylthiophene-2-carboxylic acidHCID 27600835-Methylthiophene-2-carbonyl chlorideHCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]anilineHCID 21890540HCID 21890540, compound

Product 1

HCID 21890294HCID 21890294, compoundYield 52%

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 5-methyl-2-thiophenecarboxylic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 5-methyl-2-thiophenecarbonyl isothiocyanate was prepared using the resultant 5-methyl-2-thiophenecarbonyl 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 5-methyl-2-thiophenecarbonyl 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 (42 mg, yield 52%).

Workup

  1. customThe solvent was removed by distillation, and 5-methyl-2-thiophenecarbonyl isothiocyanate
  2. customwas prepared
  3. concentrationThe reaction solution was concentrated
  4. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-b9082a52cbc64c5ca30a21ed214d03b3
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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