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

HRID 512444Notes

Reaction equation

HRID 512444 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 96.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of potassium ethyl xanthate (16.0 g, 0.1 mol) and 2-amino-4-methylphenol (12.3 g, 0.1 mol) was dissolved in absolute ethanol (150 mL). The mixture was stirred at reflux overnight. After cooling, the reaction solvent was evaporated under reduced pressure. The resultant residue was dissolved in water (200 mL) and treated with HOAc to pH to 5. The resultant solid was filtered and dried to afford 5-methyl-2-mercaptobenzoxazole (16.0 g, 96% yield).

Workup

  1. temperatureat reflux overnight
  2. temperatureAfter cooling
  3. customthe reaction solvent was evaporated under reduced pressure
  4. dissolutionThe resultant residue was dissolved in water (200 mL)
  5. additiontreated with HOAc
  6. filtrationThe resultant solid was filtered
  7. customdried

Sources & evidence

ORD record
ord-52fc27ad97aa46f4a6ea70432b5a6e96
Source dataset
uspto-grants-2015_08
Patent number
US09102636B2

Reaction notes

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