Toluene → HCID 21891041, compound

HRID 721796Notes

Reaction equation

HRID 721796 reaction equation
FC1C=CC=C(F)C=1C(Cl)=O.[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[C:20]([N:22]=[C:23]=[S:24])=[O:21].[Cl:25][C:26]1[CH:27]=[C:28]([CH:30]=[CH:31][C:32]=1[O:33][C:34]1[C:43]2[C:38](=[CH:39][C:40]([O:46][CH3:47])=[C:41]([O:44][CH3:45])[CH:42]=2)[N:37]=[CH:36][CH:35]=1)[NH2:29].C1(C)C=CC=CC=1>C(O)C>[F:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([F:19])[C:14]=1[C:20]([N:22]=[C:23]=[S:24])=[O:21].[Cl:25][C:26]1[CH:27]=[C:28]([NH:29][C:23]([NH:22][C:20](=[O:21])[C:14]2[C:13]([F:12])=[CH:18][CH:17]=[CH:16][C:15]=2[F:19])=[S:24])[CH:30]=[CH:31][C:32]=1[O:33][C:34]1[C:43]2[C:38](=[CH:39][C:40]([O:46][CH3:47])=[C:41]([O:44][CH3:45])[CH:42]=2)[N:37]=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 874382,6-Difluorobenzoyl chlorideHCID 109655092,6-DifluorobenzoylisothiocyanateHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline

Product 2

HCID 109655092,6-DifluorobenzoylisothiocyanateHCID 21891041HCID 21891041, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2,6-Difluoro-1-benzenecarbonyl isothiocyanate was prepared using commercially available 2,6-difluoro-1-benzenecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 2,6-Difluoro-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 (59 mg, yield 74%). 1H-NMR (DMSO-d6, 400 MHz): δ 3.94 (s, 3H), 3.96 (s, 3H), 6.57 (d, J=4.64 Hz, 1H), 7.11–7.51 (m, 4H), 7.62–7.64 (m, 1H), 7.80–7.83 (m, 2H), 8.08 (m, 1H), 8.52 (d, J=5.12 Hz, 1H), 12.16 (s, 1H), 12.28 (s, 1H) Mass spectrometry value (ESI-MS, m/z): 530 (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-6b36ea74de934c5cbec6fa5ca46166d2
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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