4-Fluorobenzenesulfonyl chloride → HCID 18668807, compound

HRID 1058634Notes

Reaction equation

HRID 1058634 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[C:18]2[N:19]=[CH:20][N:21]([CH2:22][CH2:23][CH:24]3[CH2:29][CH2:28][NH:27][CH2:26][CH2:25]3)[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1.C(=O)([O-])[O-].[K+].[K+].[F:36][C:37]1[CH:42]=[CH:41][C:40]([S:43](Cl)(=[O:45])=[O:44])=[CH:39][CH:38]=1.[OH-].[Na+]>CN(C)C=O>[Cl:8][C:9]1[C:18]2[N:19]=[CH:20][N:21]([CH2:22][CH2:23][CH:24]3[CH2:29][CH2:28][N:27]([S:43]([C:40]4[CH:41]=[CH:42][C:37]([F:36])=[CH:38][CH:39]=4)(=[O:45])=[O:44])[CH2:26][CH2:25]3)[C:17]=2[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N:10]=1

Participants

6

Reactant 4

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 18668816HCID 18668816, compound

Product 1

HCID 18668807HCID 18668807, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of 0.50 g of 4-chloro-1-[2-(4-piperidyl)ethyl]-1H-imidazo-[4,5-c]quinoline trifluoroacetate and 0.32 g of potassium carbonate in 2 ml of N,N-dimethylformamide, a solution of 0.23 g of p-fluorobenzenesulfonyl chloride in 3 ml of N,N-dimethylformamide was added dropwise at room temperature, and the mixture was stirred for 5 hours. The reaction mixture was adjusted to pH 10 with 10% aqueous sodium hydroxide solution, and extracted with ethyl acetate. The extract was washed successively with water and saturated brine, and dried, and then the solvent was evaporated to give 0.35 g of a colorless solid. Recrystallization from a mixture of methanol, ethanol and water gave colorless crystals having the melting point of from 175 to 178.5° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed successively with water and saturated brine
  3. customdried
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-5085c093352d423d8b26984b661d060d
Source dataset
uspto-grants-2003_02
Patent number
US06518265B1

Reaction notes

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