Potassium ethylxanthate → HCID 178526504, compound

HRID 512449Notes

Reaction equation

HRID 512449 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+]>C(O)C>[SH:14][C:13]1[O:11][C:3]2[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 2735045Potassium ethylxanthateHCID 36133892-Amino-4-Nitrophenol

Product 1

HCID 178526504HCID 178526504, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-amino-4-nitrophenol (12.5 g, 71 mmol) and potassium ethyl xanthate (13 g, 81 mmol) were dissolved in ethanol (200 mL). The reaction was heated at reflux overnight. After cooling, solvent in the reaction mixture was evaporated under reduced pressure. The resultant residue was dissolved in water and adjusted to pH 2-3 with 2N HCl, resulting in the formation of a red solid. The red solid was filtered giving 2-mercapto-5-nitrobenzoxazole (10.6 g, 76%).

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux overnight
  3. temperatureAfter cooling
  4. customsolvent in the reaction mixture was evaporated under reduced pressure
  5. dissolutionThe resultant residue was dissolved in water
  6. customresulting in the formation of a red solid
  7. filtrationThe red solid was filtered

Sources & evidence

ORD record
ord-6351ae6f9b39497492e1d1f0d41072ff
Source dataset
uspto-grants-2015_08
Patent number
US09102636B2

Reaction notes

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