4-Aminophenol → 4-(Benzo[d]thiazol-2-ylamino)phenol

HRID 410167Notes

Reaction equation

HRID 410167 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]([OH:18])=[CH:14][CH:13]=1>CN1CCCC1=O>[S:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 119872-Chlorobenzothiazole

Product 1

HCID 593268134-(Benzo[d]thiazol-2-ylamino)phenol

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The solution of 2-chlorobenzothiazole (2.47 mL, 20 mmol) and 4-aminophenol (2.18 g, 20.0 mmol) in N-methylpyrrolidone (16 mL) was heated at 160° C. for 7 h. The reaction mixture was quenched with aqueous 2N NaOH and then extracted with EtOAc. The organic layer was washed with 2N NaOH. To the combined aqueous layer was added aqueous 5N HCl until pH 6, then the product was extracted with EtOAc (2×), dried (Na2SO4) and concentrated. The crude product was dissolved in MeOH and treated with SiO2. Chromatography through a Redi-Sep® pre-packed silica gel column (120 g), eluting with a gradient of 0% to 50% EtOAc in hexane, provided 4-(benzo[d]thiazol-2-ylamino)phenol as a tan solid.

Workup

  1. customThe reaction mixture was quenched with aqueous 2N NaOH
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with 2N NaOH
  4. additionTo the combined aqueous layer was added aqueous 5N HCl until pH 6
  5. extractionthe product was extracted with EtOAc (2×)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. dissolutionThe crude product was dissolved in MeOH
  9. additiontreated with SiO2
  10. washChromatography through a Redi-Sep® pre-packed silica gel column (120 g), eluting with a gradient of 0% to 50% EtOAc in hexane

Sources & evidence

ORD record
ord-1c45d22c4b0445029def4bcc2baffcb6
Source dataset
uspto-grants-2014_06
Patent number
US08759532B2

Reaction notes

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