4-Phenylbenzoyl chloride → HCID 21890549, compound

HRID 721898Notes

Reaction equation

HRID 721898 reaction equation
C1(C2C=CC(C(Cl)=O)=CC=2)C=CC=CC=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:27]=1[O:28][CH3:29])[N:24]=[CH:23][CH:22]=[C:21]2[O:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[C:33]([F:38])[CH:32]=1.[C:39]1([C:45]2[CH:50]=[CH:49][C:48]([C:51]([N:53]=[C:54]=[S:55])=[O:52])=[CH:47][CH:46]=2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C1(C)C=CC=CC=1.C(O)C>[C:39]1([C:45]2[CH:50]=[CH:49][C:48]([C:51]([N:53]=[C:54]=[S:55])=[O:52])=[CH:47][CH:46]=2)[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1.[C:39]1([C:45]2[CH:50]=[CH:49][C:48]([C:51]([NH:53][C:54]([NH:35][C:34]3[CH:36]=[CH:37][C:31]([O:30][C:21]4[C:20]5[C:25](=[CH:26][C:27]([O:28][CH3:29])=[C:18]([O:17][CH3:16])[CH:19]=5)[N:24]=[CH:23][CH:22]=4)=[CH:32][C:33]=3[F:38])=[S:55])=[O:52])=[CH:47][CH:46]=2)[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1

Participants

7

Reactant 3

HCID 841514-Phenylbenzoyl chlorideHCID 113014704-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroanilineHCID 1247221167132-17-6

Product 2

HCID 1247221167132-17-6HCID 21890549HCID 21890549, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

4-Phenyl-1-benzenecarbonyl isothiocyanate was prepared using commercially available 4-phenyl-1benzenecarbonyl chloride (80 mg) as a starting compound according to the description of the literature. 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-2-fluoroaniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 4-phenyl-1-benzenecarbonyl isothiocyanate in ethanol (1 ml) was then 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 (41 mg, yield 47%).

Workup

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

Sources & evidence

ORD record
ord-84744b75d8a4473092456184a5884a3b
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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