2-Amino-4-chlorophenol → HCID 178527795, compound

HRID 512442Notes

Reaction equation

HRID 512442 reaction equation
O(CC)[C:2]([S-])=[S:3].[K+].[Cl:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([NH2:16])[CH:10]=1>C(O)C>[Cl:8][C:9]1[CH:14]=[CH:13][C:12]2[O:15][C:2]([SH:3])=[N:16][C:11]=2[CH:10]=1

Participants

4

Reactant 2

HCID 72652-Amino-4-chlorophenolHCID 2735045Potassium ethylxanthate

Product 1

HCID 178527795HCID 178527795, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of potassium ethyl xanthate (13.4 g, 84.0 mmol) and 4-chloro-2-aminophenol (10 g, 69.6 mmol) was dissolved in absolute ethanol (200 mL). The mixture was stirred under reflux overnight. After cooling, the solvent was evaporated under reduced pressure, the residue was dissolved in water (200 mL) and treated with HOAc to adjust pH to 5. A solid formed, which was filtered and dried to afford 5-chloro-2-mercaptobenzoxazole (12.8 g, yield 99.1%).

Workup

  1. temperatureunder reflux overnight
  2. temperatureAfter cooling
  3. customthe solvent was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in water (200 mL)
  5. additiontreated with HOAc
  6. customA solid formed
  7. filtrationwhich was filtered
  8. customdried

Sources & evidence

ORD record
ord-333a50b1313d4f728f291bcb92d393b9
Source dataset
uspto-grants-2015_08
Patent number
US09102636B2

Reaction notes

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