Toluene → HCID 21890391, compound

HRID 721811Notes

Reaction equation

HRID 721811 reaction equation
O1C=CC=C1C(Cl)=O.[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]([N:16]=[C:17]=[S:18])=[O:15].[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][C:30]=1[O:31][CH3:32])[N:27]=[CH:26][CH:25]=[C:24]2[O:33][C:34]1[CH:40]=[CH:39][C:37]([NH2:38])=[C:36]([F:41])[CH:35]=1.C1(C)C=CC=CC=1>C(O)C>[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]([N:16]=[C:17]=[S:18])=[O:15].[CH3:19][O:20][C:21]1[CH:22]=[C:23]2[C:28](=[CH:29][C:30]=1[O:31][CH3:32])[N:27]=[CH:26][CH:25]=[C:24]2[O:33][C:34]1[CH:40]=[CH:39][C:37]([NH:38][C:17]([NH:16][C:14]([C:10]2[O:9][CH:13]=[CH:12][CH:11]=2)=[O:15])=[S:18])=[C:36]([F:41])[CH:35]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 682422-Furancarbonyl chlorideHCID 27592432-Furoyl isothiocyanateHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline

Product 2

HCID 27592432-Furoyl isothiocyanateHCID 21890391HCID 21890391, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-Furancarbonyl isothiocyanate was prepared using commercially available 2-furancarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 2-Furancarbonyl 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 (47 mg, yield 68%). Mass spectrometry value (ESI-MS, m/z): 468 (M++1)

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-c9933a424dfb4a5aa31923af2495b6e6
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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