Thiophenol → HCID 89675021, compound

HRID 1186734Notes

Reaction equation

HRID 1186734 reaction equation
[O:1]=[C:2]1[NH:11][C:10]2[C:9]3[CH2:12][CH2:13][CH2:14][CH2:15][C:8]=3[CH:7]=[CH:6][C:5]=2[N:4]([C:16]2[CH:17]=[C:18]([N:22]([CH3:35])S(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[CH:19]=[CH:20][CH:21]=2)[C:3]1=[O:36].C1(S)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+].[ClH:50].CO>C(Cl)(Cl)Cl.CO.CN(C=O)C>[ClH:50].[CH3:35][NH:22][C:18]1[CH:17]=[C:16]([N:4]2[C:5]3[CH:6]=[CH:7][C:8]4[CH2:15][CH2:14][CH2:13][CH2:12][C:9]=4[C:10]=3[NH:11][C:2](=[O:1])[C:3]2=[O:36])[CH:21]=[CH:20][CH:19]=1

Participants

8

Reactant 4

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 21893726Hydrochloride methanolHCID 89674887HCID 89674887, compound

Product 1

HCID 89675021HCID 89675021, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of N-[3-(2,3-dioxo-2,3,7,8,9,10-hexahydrobenzo[f]quinoxalin-4(1H)-yl)phenyl]-N-methyl-2-nitrobenzenesulfonamide (35 mg, 0.070 mmol), thiophenol (8.5 μL, 0.083 mmol), potassium carbonate (29 mg, 0.210 mmol), and dry DMF (1 mL) was stirred at room temperature for 18 hours. To the reaction solution was added ice-cold water. The precipitated crystal was collected by filtration, washed with water, and dried. The obtained crude compound was suspended in a methanol (1 mL) and 2M hydrogen chloride/methanol solution (40 μL). To the suspension was added chloroform to form a solution. The solvent was removed by evaporation under reduced pressure. To the obtained residue was added water, and concentrated again to obtain the titled compound as a pale yellow crystal (15 mg, yield 71%).

Workup

  1. additionTo the reaction solution was added ice-cold water
  2. filtrationThe precipitated crystal was collected by filtration
  3. washwashed with water
  4. customdried
  5. customThe obtained crude compound
  6. customto form a solution
  7. customThe solvent was removed by evaporation under reduced pressure
  8. additionTo the obtained residue was added water
  9. concentrationconcentrated again

Sources & evidence

ORD record
ord-734b22c7ac07449fa2d830863a301e15
Source dataset
uspto-grants-2014_03
Patent number
US08673915B2

Reaction notes

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