Toluene → HCID 21890220, compound

HRID 721807Notes

Reaction equation

HRID 721807 reaction equation
C(OCC(Cl)=O)C1C=CC=CC=1.[CH2:13]([O:20][CH2:21][C:22]([N:24]=[C:25]=[S:26])=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:27][O:28][C:29]1[CH:30]=[C:31]2[C:36](=[CH:37][C:38]=1[O:39][CH3:40])[N:35]=[CH:34][CH:33]=[C:32]2[O:41][C:42]1[CH:48]=[CH:47][C:45]([NH2:46])=[C:44]([F:49])[CH:43]=1.C1(C)C=CC=CC=1>C(O)C>[CH2:13]([O:20][CH2:21][C:22]([N:24]=[C:25]=[S:26])=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH2:13]([O:20][CH2:21][C:22]([NH:24][C:25]([NH:46][C:45]1[CH:47]=[CH:48][C:42]([O:41][C:32]2[C:31]3[C:36](=[CH:37][C:38]([O:39][CH3:40])=[C:29]([O:28][CH3:27])[CH:30]=3)[N:35]=[CH:34][CH:33]=2)=[CH:43][C:44]=1[F:49])=[S:26])=[O:23])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 177085Benzyloxyacetyl chlorideHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroanilineHCID 21890697HCID 21890697, compound

Product 2

HCID 21890220HCID 21890220, compoundYield 43%HCID 21890697HCID 21890697, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

2-(Benzyloxy)ethanoyl isothiocyanate was prepared using commercially available 2-(benzyloxy)ethanoyl chloride (80 mg) as a starting compound according to the description of the literature. 2-(Benzyloxy)ethanoyl 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 (38 mg, yield 43%). Mass spectrometry value (ESI-MS, m/z): 522 (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-8695c3de96eb46ee98f983c6f192c7b7
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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