Bromic acid → 2-[6-(methylamino)pyridin-3-yl]-1,3-benzothiazol-6-ol

HRID 2276911Notes

Reaction equation

HRID 2276911 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[CH:17]=[C:16]([O:18]C)[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][N:4]=1.Br(O)(=O)=O.C(=O)(O)[O-].[Na+]>O>[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:10][C:11]3[CH:17]=[C:16]([OH:18])[CH:15]=[CH:14][C:12]=3[N:13]=2)=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 24445Bromic acidHCID 516892Sodium BicarbonateHCID 24803723HCID 24803723, compound

Product 1

HCID 166632752-[6-(methylamino)pyridin-3-yl]-1,3-benzothiazol-6-olYield 89.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-[2-(N-Monomethyl)aminopyridin-5-yl]-6-methoxybenzothiazole (42, 650 mg, 2.40 mmol) obtained in step 3 was dissolved in [bmim][BF4] (13 mL) and, after adding bromic acid (48%, 2.4 mL), the reaction mixture was held at 130° C. overnight. After cooling to room temperature and adding water and sodium bicarbonate aqueous solution, the solid thus obtained was filtered and washed with water. After removing the solvent under reduced pressure, recrystallization from methanol and dichloromethane solvent yielded 2-[2-(N-monomethyl)aminopyridin-5-yl]-6-hydroxybenzothiazole (46, 550 mg, 89%) as a brown solid.

Workup

  1. customthe solid thus obtained
  2. filtrationwas filtered
  3. washwashed with water
  4. customAfter removing the solvent
  5. customunder reduced pressure, recrystallization from methanol and dichloromethane solvent

Sources & evidence

ORD record
ord-b329986a356f4a2a8715f6e70370a61b
Source dataset
uspto-grants-2015_09
Patent number
US09133143B2

Reaction notes

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