Water → HCID 19592369, compound

HRID 613512Notes

Reaction equation

HRID 613512 reaction equation
[SH:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:14][C:15]1[C:24]2[C:19](=[C:20]([NH:25][C:26](=[O:35])[C:27]3[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][C:28]=3[Cl:34])[CH:21]=[CH:22][CH:23]=2)[N:18]=[CH:17][C:16]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37].O>CN(C)C=O>[Cl:34][C:28]1[CH:29]=[CH:30][CH:31]=[C:32]([Cl:33])[C:27]=1[C:26]([NH:25][C:20]1[CH:21]=[CH:22][CH:23]=[C:24]2[C:19]=1[N:18]=[CH:17][C:16]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:15]2[CH2:14][S:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1)=[O:35]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 19592415HCID 19592415, compoundHCID 178527877HCID 178527877, compound

Product 1

HCID 19592369HCID 19592369, compoundYield 92.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-mercaptoimidazole (27.4 mg) in dimethylformamide (1.5 ml) was added potassium carbonate (51.6 mg) under ice-cooling, and the mixture was stirred for 15 minutes at the same temperature. To the mixture was added 4-bromomethyl-8-(2,6-dichlorobenzoylamino)-3-ethoxycarbonylquinoline (120 mg) under ice-cooling, and the mixture was stirred for 1 hour at ambient temperature. To the mixture was added water under ice-cooling, and the resulting precipitate was collected by filtration and washed with water to give 8-(2,6-dichlorobenzoylamino)-3-ethoxycarbonyl-4-[(imidazol-2-yl)thiomethyl]quinoline (115 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture was stirred for 1 hour at ambient temperature
  4. temperaturecooling
  5. filtrationthe resulting precipitate was collected by filtration
  6. washwashed with water

Sources & evidence

ORD record
ord-e8a1bc6703c644638fdf1dfa39746015
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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