Ammonia → HCID 9115295, compound

HRID 1186312Notes

Reaction equation

HRID 1186312 reaction equation
[NH3:1].[F:2][C:3]([F:15])([F:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11].[Cl:16][C:17]1[C:26](Cl)=[N:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1.C(=O)([O-])[O-].[K+].[K+]>CO.C(O)(=O)C.CS(C)=O>[F:2][C:3]([F:15])([F:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:1][C:26]1[C:17]([Cl:16])=[N:18][C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[N:25]=1)(=[O:12])=[O:11]

Participants

8

Reactant 4

HCID 222AmmoniaHCID 11430Potassium CarbonateHCID 166592,3-DichloroquinoxalineHCID 1366162-Trifluoromethylbenzenesulphonyl chloride

Product 1

HCID 9115295HCID 9115295, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 887MethanolSolvent

Procedure

To a 7 mol/L solution of ammonia in methanol (4.0 mL), 2-(trifluoromethyl)benzenesulfonyl chloride (200 mg, 0.818 mmol) was added and the mixture was stirred at room temperature for 1 hour. After the reaction mixture was concentrated, 2,3-dichloroquinoxaline (162 mg, 0.818 mmol), potassium carbonate (113 mg, 0.818 mmol) and dimethyl sulfoxide (5.0 mL) were added to the residue, and the mixture was stirred at 150° C. for 1 hour. The reaction mixture was slowly added to a mixture (50 ml) of a 1% aqueous acetic acid solution and ice, and the mixture was stirred for 3 hours. The resulting solid was collected by filtration and purified by preparative thin-layer chromatography (chloroform/methanol=19/1). Further, slurry purification was performed using hexane, to give 2-(trifluoromethyl)-N-{3-chloroquinoxalin-2-yl}benzenesulfonamide (Compound AC) (97.0 mg, yield: 31%).

Workup

  1. concentrationAfter the reaction mixture was concentrated
  2. stirringthe mixture was stirred at 150° C. for 1 hour
  3. stirringthe mixture was stirred for 3 hours
  4. filtrationThe resulting solid was collected by filtration
  5. custompurified by preparative thin-layer chromatography (chloroform/methanol=19/1)
  6. customFurther, slurry purification

Sources & evidence

ORD record
ord-3fe80cb9321a416faa8b5c88a05dd1ff
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

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