Thionyl Chloride → HCID 21890013, compound

HRID 721590Notes

Reaction equation

HRID 721590 reaction equation
S(Cl)(Cl)=O.BrC1SC(C(O)=O)=CC=1.BrC1SC(C(Cl)=O)=CC=1.[Br:23][C:24]1[S:28][C:27]([C:29]([N:31]=[C:32]=[S:33])=[O:30])=[CH:26][CH:25]=1.[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>[Br:23][C:24]1[S:28][C:27]([C:29]([NH:31][C:32]([NH:38][C:37]2[CH:39]=[CH:40][C:41]([O:42][C:43]3[C:52]4[C:47](=[CH:48][C:49]([O:55][CH3:56])=[C:50]([O:53][CH3:54])[CH:51]=4)[N:46]=[CH:45][CH:44]=3)=[C:35]([Cl:34])[CH:36]=2)=[S:33])=[O:30])=[CH:26][CH:25]=1

Participants

8

Reactant 5

HCID 24386Thionyl ChlorideHCID 3491155-Bromothiophene-2-carboxylic acidHCID 6057125-Bromothiophene-2-carbonyl chlorideHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 21891177HCID 21891177, compound

Product 1

HCID 21890013HCID 21890013, compoundYield 75%

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-bromo-2-thiophenecarboxylic acid (80 mg), and the mixture was heated at 100° C. for one hr. The solvent was removed by distillation, and 5-bromo-2-thiophene isothiocyanate was prepared using the resultant 5-bromo-2-thiophenecarbonyl chloride as a starting compound according to the description of the literature. 5-Bromo-2-thiophenecarbonyl 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 18 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 (65 mg, yield 75%).

Workup

  1. customThe solvent was removed by distillation, and 5-bromo-2-thiophene 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-a2987702bf47409f8617fc1cda42f3b9
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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