Carbon Disulfide → 7-Aminobenzo[D]oxazole-2-thiol

HRID 1783493Notes

Reaction equation

HRID 1783493 reaction equation
[OH-].[K+].[C:3](=[S:5])=S.[NH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH2:13])[C:8]=1[OH:14]>CCO.O>[NH2:6][C:7]1[C:8]2[O:14][C:3](=[S:5])[NH:13][C:9]=2[CH:10]=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 14797Potassium HydroxideHCID 5800102,6-Diaminophenol

Product 1

HCID 575905387-Aminobenzo[D]oxazole-2-thiolYield 49.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of KOH (0.875 g, 15.6 mmol) in EtOH (14.3 mL) and water (2.6 mL) was treated with carbon disulfide (0.828 g, 10.9 mmol), followed by of 2,6-diaminophenol (1.50 g, 12.1 mmol). The mixture was heated at reflux temperature for 3 h, concentrated, neutralized with 1M HCl to pH 7, and extracted with EtOAc. The extracts were combined, dried over Na2SO4 and concentrated in vacuo to afford the title compound (0.90 g, 45%), characterized by NMR and mass spectral analyses.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux temperature for 3 h
  3. concentrationconcentrated
  4. extractionextracted with EtOAc
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-33955f38fde54746bd39becf7c2eed71
Source dataset
uspto-grants-2009_03
Patent number
US07501421B2

Reaction notes

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