Water → HCID 19592982, compound

HRID 613495Notes

Reaction equation

HRID 613495 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1Cl)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:13][C:14](=[O:23])[C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:22].[SH:24][C:25]1[NH:26][CH:27]=[CH:28][N:29]=1.C(=O)([O-])[O-].[K+].[K+].O>CN1CCCC1=O>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[S:24][C:25]1[NH:26][CH:27]=[CH:28][N:29]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[NH:13][C:14](=[O:23])[C:15]1[C:20]([Cl:21])=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:22]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 19592487HCID 19592487, compoundHCID 178527877HCID 178527877, compound

Product 1

HCID 19592982HCID 19592982, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 3-bromo-4-chloro-8-(2,6-dichlorobenzoylamino)quinoline (120 mg) in N-methylpyrrolidone were added 2-mercaptoimidazole (33.5 mg) and potassium carbonate (50.1 mg), and the mixture was stirred for 40 minutes at ambient temperature, for 1 hour at 40° C., for 1 hour at 80° C. and for 1 hour at 90° C. To the mixture was added water, and the resulting precipitate was collected by filtration and washed with water and ethanol to give 3-bromo-8-(2,6-dichlorobenzoylamino)-4-(imidazol-2-ylthio)quinoline (88.0 mg).

Workup

  1. filtrationthe resulting precipitate was collected by filtration
  2. washwashed with water and ethanol

Sources & evidence

ORD record
ord-7a01e82c31034adb8d768706f3b4d1c6
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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