4-Aminothiophenol → HCID 18971644, compound

HRID 55086Notes

Reaction equation

HRID 55086 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:5]=2[N:6]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([SH:19])=[CH:15][CH:14]=1>CN(C1C=CN=CC=1)C.C(O)C>[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([S:19][C:2]2[S:3][C:4]3[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][C:5]=3[N:6]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 2

HCID 145104-AminothiophenolHCID 133148162,5-Dichloro-1,3-benzothiazole

Product 1

HCID 18971644HCID 18971644, compoundYield 22.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent

Procedure

2,5-Dichlorobenzothiazole (0.049 moles, 10.0 g), 4-aminothiophenol (0.049 moles, 6.1 g) and DMAP (0.049 moles, 6.0 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 25% ethyl acetate in hexane to yield 2-(4-aminophenylthio)-5-chlorobenzothiazole 3.2 g, 22%. Mass spec (FD) 292. Calculated for C13H9ClN2S2 : C, 53.33; H, 3.10; N, 9.57. Found: C, 53.03; H, 3.30; N, 9.70.

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 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-1649a1ff85014499b6bc5f0bbaec4e76
Source dataset
uspto-grants-1997_04
Patent number
US05624937

Reaction notes

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