4-Aminothiophenol → 4-(6-Chloro-2-quinoxalylthio)-aniline

HRID 354632

Reaction equation

HRID 354632 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([SH:8])=[CH:4][CH:3]=1.[OH-].[K+].NC1C=CC([S-])=CC=1.[K+].Cl[C:21]1[CH:30]=[N:29][C:28]2[C:23](=[CH:24][CH:25]=[C:26]([Cl:31])[CH:27]=2)[N:22]=1>CS(C)=O.O>[Cl:31][C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[N:22]=[C:21]([S:8][C:5]1[CH:6]=[CH:7][C:2]([NH2:1])=[CH:3][CH:4]=1)[CH:30]=[N:29]2

Participants

7

Reactant 4

HCID 145104-AminothiophenolHCID 14797Potassium HydroxideHCID 877482,6-DichloroquinoxalineHCID 11816037Potassium p-aminothiophenolate

Product 1

HCID 131089424-(6-Chloro-2-quinoxalylthio)-anilineYield 52%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent2×

Procedure

5.7 g (0.045 mol) of p-aminothiophenol together with 3 g (0.045 mol) of 86% potassium hydroxide and 2 ml of water in 80 ml of dimethylsulfoxide was heated under stirring at 80°-90° C. for 5 hours to make the potassium p-aminothiophenolate. The water generated was removed off by azeotropic distillation under reduced pressure. To this solution which was allowed to be cooled to room temperature was added a solution of 9 g (0.045 mol) of 2,6-dichloroquinoxaline dissolved in 100 ml of dimethylsulfoxide. The mixture was subjected to the reaction, while stirring, at 80°-90° C. for 8 hours. After the reaction mixture was cooled to the room temperature, it was poured into a great deal of water and stirred. The precipitating solid was filtered off, washed with 5% aqueous solution of sodium hydroxide and then washed with water, followed by drying. The crude crystals thus obtained were recrystallized from a mixed solution of ethanol-benzene to produce 6.7 g (yield 52%) of the intended compound (Compound No. 10) as light-yellow crystals, m.p. 144°-147° C.

Workup

  1. customThe water generated was removed off by azeotropic distillation under reduced pressure
  2. customThe mixture was subjected to the reaction
  3. stirringwhile stirring, at 80°-90° C. for 8 hours
  4. temperatureAfter the reaction mixture was cooled to the room temperature, it
  5. stirringstirred
  6. filtrationThe precipitating solid was filtered off
  7. washwashed with 5% aqueous solution of sodium hydroxide
  8. washwashed with water
  9. customby drying
  10. customThe crude crystals thus obtained
  11. customwere recrystallized from a mixed solution of ethanol-benzene

Sources & evidence

ORD record
ord-bbabf4cdcf4d43369b8907aa8c120dd8
Source dataset
uspto-grants-1983_03
Patent number
US04376202

Linked notes

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