Toluene → HCID 21890965, compound

HRID 721828Notes

Reaction equation

HRID 721828 reaction equation
N1(C(Cl)=O)CCOCC1.[N:10]1([C:16]([N:18]=[C:19]=[S:20])=[O:17])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[Cl:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][C:28]=1[O:29][C:30]1[C:39]2[C:34](=[CH:35][C:36]([O:42][CH3:43])=[C:37]([O:40][CH3:41])[CH:38]=2)[N:33]=[CH:32][CH:31]=1)[NH2:25].C1(C)C=CC=CC=1>C(O)C>[N:10]1([C:16]([N:18]=[C:19]=[S:20])=[O:17])[CH2:11][CH2:12][O:13][CH2:14][CH2:15]1.[Cl:21][C:22]1[CH:23]=[C:24]([NH:25][C:19]([NH:18][C:16]([N:10]2[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)=[O:17])=[S:20])[CH:26]=[CH:27][C:28]=1[O:29][C:30]1[C:39]2[C:34](=[CH:35][C:36]([O:42][CH3:43])=[C:37]([O:40][CH3:41])[CH:38]=2)[N:33]=[CH:32][CH:31]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 848104-Morpholinecarbonyl chlorideHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 13441037HCID 13441037, compound

Product 2

HCID 13441037HCID 13441037, compoundHCID 21890965HCID 21890965, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

4-Morpholinecarbonyl isothiocyanate was prepared using commercially available 4-morpholinecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 4-Morpholinecarbonyl 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 (40 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-b5a1eabc37a44ac8ad61b46cc42f6bf0
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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