Tetrahydrofuran → HCID 67466593, compound

HRID 1845911Notes

Reaction equation

HRID 1845911 reaction equation
[Br:1][C:2]1[C:10]2[S:9][C:8](SC)=[N:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH2:13].C1C[O:17]CC1.C[O-].[Na+]>CCOC(C)=O>[NH2:13][C:3]1[CH:4]=[CH:5][C:6]2[NH:7][C:8](=[O:17])[S:9][C:10]=2[C:2]=1[Br:1]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10942334Sodium MethoxideHCID 67468620HCID 67468620, compound

Product 1

HCID 67466593HCID 67466593, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a round bottom flask was added 7-bromo-2-(methylthio)-1,3-benzothiazol-6-amine (13-1) (0.600 g, 2.180 mmol), THF (20 mL), and solid sodium methoxide (0.471 g, 8.72 mmol). The reaction mixture was then stirred at room temperature for several hours followed by heating to 60 C in a hot oil bath with stirring for several hours, then to 90 C for several hours. The reaction mixture was then suspended in EtOAc, washed with sat'd NaHCO3, then water, then brine. Organics were then dried over Na2SO4 filtered & concentrated to give 6-amino-7-bromo-1,3-benzothiazol-2(3H)-one (13-2) as a tan solid. HRMS (M+H)+: observed=244.9379, calculated=244.9379.

Workup

  1. temperatureby heating to 60 C in a hot oil bath
  2. stirringwith stirring for several hours
  3. waitto 90 C for several hours
  4. washwashed with sat'd NaHCO3
  5. dry with materialOrganics were then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-252a81a460724f1cac1199808b961e52
Source dataset
uspto-grants-2015_02
Patent number
US08952005B2

Reaction notes

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