Potassium Carbonate → 4-(2-Benzothiazol-2-ylthio)aniline

HRID 55084

Reaction equation

HRID 55084 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([SH:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+]>C(O)C>[NH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][C:2]2[S:3][C:4]3[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=3[N:6]=2)=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 119872-ChlorobenzothiazoleHCID 145104-Aminothiophenol

Product 1

HCID 1176104-(2-Benzothiazol-2-ylthio)anilineYield 88.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-Chlorobenzothiazole (0.06 moles, 10.1 g), 4-aminothiophenol (0.06 moles, 7.5 g) and potassium carbonate (0.06 moles, 8.3 g) were stirred for 3 days at room temperature in 250 ml ethanol, filtered, and concentrated. Ethyl acetate was added and the solution washed with water, dried over sodium sulfate and concentrated. The product was purified by HPLC over silica gel eluted with 40-60% ethyl acetate in hexane to yield 2-(4-aminophenylthio)benzothiazole 13.7 g, 88%. Mass spec (FD) 258. Calculated for C11H10N2S2:C, 60.44; H, 3.90; N, 10.84. Found: C, 60.63; H, 3.98; N, 11.01.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated
  3. additionEthyl acetate was added
  4. washthe solution washed with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customThe product was purified by HPLC over silica gel
  8. washeluted with 40-60% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d19d97a641a448f4938338c0b9f8cf75
Source dataset
uspto-grants-1997_04
Patent number
US05624937

Linked notes

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