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

HRID 1174915Notes

Reaction equation

HRID 1174915 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].CCO[C:15]([S-])=[S:16].[K+].Cl>N1C=CC=CC=1>[N+:8]([C:6]1[CH:5]=[CH:4][C:3]2[O:11][C:15](=[S:16])[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 79.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Combine 2-amino-4-nitrophenol (15.8 g, 102 mmol) and potassium xanthate (18.2 g, 114 mmol) in pyridine (200 mL). Reflux for 1 hour and then cool to room temperature. Pour the reaction into concentrated HCl (100 mL) and ice. Filter and wash the product with 1 N HCl to remove excess pyridine. Dry in a vacuum oven at 50° C. for 48 h to afford the title compound (15.9 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. temperatureReflux for 1 hour
  2. additionPour
  3. filtrationFilter
  4. washwash the product with 1 N HCl
  5. customto remove excess pyridine
  6. customDry in a vacuum oven at 50° C. for 48 h

Sources & evidence

ORD record
ord-ff9778e49fac416ba84ea4044c28794e
Source dataset
uspto-grants-2010_11
Patent number
US07838543B2

Reaction notes

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