Toluene → HCID 21891113, compound

HRID 721834Notes

Reaction equation

HRID 721834 reaction equation
C1(C(Cl)=O)CC1.[CH:7]1([C:10]([N:12]=[C:13]=[S:14])=[O:11])[CH2:9][CH2:8]1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[O:23][C:24]1[C:33]2[C:28](=[CH:29][C:30]([O:36][CH3:37])=[C:31]([O:34][CH3:35])[CH:32]=2)[N:27]=[CH:26][CH:25]=1)[NH2:19].C1(C)C=CC=CC=1>C(O)C>[CH:7]1([C:10]([N:12]=[C:13]=[S:14])=[O:11])[CH2:9][CH2:8]1.[Cl:15][C:16]1[CH:17]=[C:18]([NH:19][C:13]([NH:12][C:10]([CH:7]2[CH2:9][CH2:8]2)=[O:11])=[S:14])[CH:20]=[CH:21][C:22]=1[O:23][C:24]1[C:33]2[C:28](=[CH:29][C:30]([O:36][CH3:37])=[C:31]([O:34][CH3:35])[CH:32]=2)[N:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 77637Cyclopropanecarbonyl chlorideHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 16792372Cyclopropanecarbonyl isothiocyanate

Product 2

HCID 16792372Cyclopropanecarbonyl isothiocyanateHCID 21891113HCID 21891113, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1-Cyclopropanecarbonyl isothiocyanate was prepared using commercially available 1-cyclopropanecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 1-Cyclopropanecarbonyl 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 (36 mg, yield 52%).

Workup

  1. customto prepare a solution
  2. concentrationThe reaction solution was concentrated
  3. customthe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-9e9ab426ebee4c41b211317a7745cdf5
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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