2-Amino-4-methylphenol → HCID 178423563, compound

HRID 553454Notes

Reaction equation

HRID 553454 reaction equation
O(CC)[C:2]([S-])=[S:3].[K+].[NH2:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[CH:11][C:10]=1[OH:16]>C(O)C>[CH3:15][C:13]1[CH:12]=[CH:11][C:10]2[O:16][C:2]([SH:3])=[N:8][C:9]=2[CH:14]=1

Participants

4

Reactant 2

HCID 72642-Amino-4-methylphenolHCID 2735045Potassium ethylxanthate

Product 1

HCID 178423563HCID 178423563, compoundYield 92.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium ethyl xanthate (4.4 g, 27.5 mmol.) was added to solution of 2-amino-4-methyl-phenol (2 g, 16.2 mmol.) in ethanol (40 mL). The reaction mixture was heated at reflux for 4 h then allowed to cool to rt. Upon cooling to rt the mixture was concentrated and the resulting residue was dissolved in water. Acetic acid was added until pH=5 and a white solid precipitated from the solution. The solid was collected by filtration, washed with water and dried to afford 5-methylbenzo[d]oxazole-2-thiol as a powder (2.4 g, 92.3%) which was used without further purification. MS (ESI) m/e (M+H+) 166.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 4 h
  3. temperatureUpon cooling to rt the mixture
  4. concentrationwas concentrated
  5. dissolutionthe resulting residue was dissolved in water
  6. additionAcetic acid was added until pH=5
  7. customa white solid precipitated from the solution
  8. filtrationThe solid was collected by filtration
  9. washwashed with water
  10. customdried

Sources & evidence

ORD record
ord-9379a1a4b6f24f9287e66ee84d70af16
Source dataset
uspto-grants-2011_11
Patent number
US08048862B2

Reaction notes

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