1,3-Benzodioxole-5-carbonyl chloride → N-(1,3-Benzodioxol-5-ylcarbonyl)-N'-{3-chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thiourea

HRID 721899Notes

Reaction equation

HRID 721899 reaction equation
O1C2C=CC(C(Cl)=O)=CC=2OC1.[Cl:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[O:21][C:22]1[C:31]2[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=2)[N:25]=[CH:24][CH:23]=1)[NH2:17].[O:36]1[C:40]2[CH:41]=[CH:42][C:43]([C:45]([N:47]=[C:48]=[S:49])=[O:46])=[CH:44][C:39]=2[O:38][CH2:37]1>C1(C)C=CC=CC=1.C(O)C>[O:36]1[C:40]2[CH:41]=[CH:42][C:43]([C:45]([N:47]=[C:48]=[S:49])=[O:46])=[CH:44][C:39]=2[O:38][CH2:37]1.[O:36]1[C:40]2[CH:41]=[CH:42][C:43]([C:45]([NH:47][C:48]([NH:17][C:16]3[CH:18]=[CH:19][C:20]([O:21][C:22]4[C:31]5[C:26](=[CH:27][C:28]([O:34][CH3:35])=[C:29]([O:32][CH3:33])[CH:30]=5)[N:25]=[CH:24][CH:23]=4)=[C:14]([Cl:13])[CH:15]=3)=[S:49])=[O:46])=[CH:44][C:39]=2[O:38][CH2:37]1

Participants

7

Reactant 3

HCID 27347491,3-Benzodioxole-5-carbonyl chlorideHCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]anilineHCID 21889895HCID 21889895, compound

Product 2

HCID 21889895HCID 21889895, compoundHCID 58738947N-(1,3-Benzodioxol-5-ylcarbonyl)-N'-{3-chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}thioureaYield 58%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 1140TolueneSolvent

Procedure

1,3-Benzodioxole-5-carbonyl isothiocyanate was prepared using commercially available 1,3-benzodioxole-5-carbonyl chloride (80 mg) as a starting compound according to the description of the literature. 3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline (50 mg) was dissolved in toluene (5 ml) and ethanol (1 ml) to prepare a solution. A solution of 1,3-benzodioxole-5-carbonyl 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 (47 mg, yield 58%).

Workup

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

Sources & evidence

ORD record
ord-9cc17c0deb574556afb2f06bf213da12
Source dataset
uspto-grants-2006_11
Patent number
US07135466B2

Reaction notes

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