4-Aminophenol → HCID 59351415, compound

HRID 887401Notes

Reaction equation

HRID 887401 reaction equation
Cl[C:2]1[S:3][C:4]2[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.[NH2:12][C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1>CN1C(=O)CCC1>[F:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)[S:3][C:4]=2[CH:10]=1

Participants

4

Reactant 2

HCID 4034-AminophenolHCID 20498702-Chloro-6-fluorobenzothiazole

Product 1

HCID 59351415HCID 59351415, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

2-Chloro-6-fluorobenzo[d]thiazole (7.0 g, 0.037 mol) and 4-aminophenol (4.0 g, 0.037 mol) in NMP (50 mL) was heated at 160° C. for 7 h. The reaction was quenched with 2N NaOH (100 mL) and then extracted with EtOAc (2×100 mL). The organic layer was washed with 2 N NaOH (50 mL) and to the combined aqueous layer was added 5 N HCl until pH 6 and then extracted with EtOAc (3×200 mL). The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated. The crude was purified by column chromatography (silica gel 100-200 mesh; 80% ethyl acetate in hexanes) to afford 4-(6-fluorobenzo[d]thiazol-2-ylamino)phenol as a white solid.

Workup

  1. customThe reaction was quenched with 2N NaOH (100 mL)
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe organic layer was washed with 2 N NaOH (50 mL) and to the combined aqueous layer
  4. additionwas added 5 N HCl until pH 6
  5. extractionextracted with EtOAc (3×200 mL)
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated
  9. customThe crude was purified by column chromatography (silica gel 100-200 mesh; 80% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-6d23a0c620494441aba3a7c782e110b2
Source dataset
uspto-grants-2012_08
Patent number
US08247418B2

Reaction notes

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