2-Aminothiophenol → benzothiazole, 2-(4-pyridinyl)-

HRID 1457813Notes

Reaction equation

HRID 1457813 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[SH:8].[N:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1>CS(C)=O>[S:8]1[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[N:1]=[C:15]1[C:12]1[CH:13]=[CH:14][N:9]=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 87132-AminothiophenolHCID 133894-Pyridinecarboxaldehyde

Product 1

HCID 236319benzothiazole, 2-(4-pyridinyl)-Yield 85%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-Aminothiophenol (6.3 g, 0.05 mol) and 4-pyridinecarboxaldehyde (5.4 g, 0.05 mol) were dissolved in dimethylsulfoxide (35 ml) and heated until vapours distilled off at 180°-186° C. The distillation residue on cooling was partitioned between ethyl acetate and saturated ammonium chloride solution. The combined organic layers were washed with water (100 ml), dried (MgSO4) and concentrated. The solid was triturated with ether to afford the title compound as a pale brown solid (9 g, 85%). δH (CDCl3), 7.42 (1H, m, ArH), 7.51 (1H, m, ArH), 7.93 (3H, m, ArH), 8.13 (1H, d, J 8.7Hz, ArH), 8.78 (2H, m, ArH). m/z (ES+) 213 (M+1)+.

Workup

  1. temperatureheated until vapours
  2. distillationdistilled off at 180°-186° C
  3. temperatureThe distillation residue on cooling
  4. customwas partitioned between ethyl acetate and saturated ammonium chloride solution
  5. washThe combined organic layers were washed with water (100 ml)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe solid was triturated with ether

Sources & evidence

ORD record
ord-a1d933703f294746bad408f7d9fe274c
Source dataset
uspto-grants-1998_12
Patent number
US05849765

Reaction notes

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