Hydrochloric Acid → 5-Nitrobenzo[D]Oxazole-2-Thiol

HRID 601545Notes

Reaction equation

HRID 601545 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].O(CC)[C:13]([S-])=[S:14].[K+].Cl>N1C=CC=CC=1>[N+:8]([C:6]1[CH:5]=[CH:4][C:3]2[O:11][C:13](=[S:14])[NH:1][C:2]=2[CH:7]=1)([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 2735045Potassium ethylxanthateHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 7862935-Nitrobenzo[D]Oxazole-2-ThiolYield 79.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Combine 2-amino-4-nitrophenol (15.8 g, 102 mmol) and potassium ethyl xanthate (18.3 g, 114 mmol) in pyridine (200 mL). Heat the reaction at reflux for 1 h. Allow the reaction to cool to room temperature and pour into concentrated HCl (100 mL) and ice. Filter and wash the solids with 1N HCl to remove excess pyridine. Dry the solids under house vacuum at 50° C. for 2 days to obtain the title compound (15.85 g, 79%). 1H NMR (400 MHz, DMSO-d6): δ 8.18 (dd, 1H, J=8.8, 2.2 Hz), 7.93 (d, 1H, J=2.2 Hz), 7.73 (d, 1H, J=8.8 Hz).

Workup

  1. temperatureHeat
  2. customthe reaction
  3. temperatureat reflux for 1 h
  4. customthe reaction
  5. filtrationFilter
  6. washwash the solids with 1N HCl
  7. customto remove excess pyridine
  8. customDry the solids under house vacuum at 50° C. for 2 days

Sources & evidence

ORD record
ord-b54021d153bd4cbfa16c077eda92d292
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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