2-Amino-4-phenylphenol → HCID 178527758, compound

HRID 2092352Notes

Reaction equation

HRID 2092352 reaction equation
[C:1]1([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([NH2:14])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O(CC)[C:16]([S-])=[S:17].[K+]>C(O)C>[C:1]1([C:7]2[CH:12]=[CH:11][C:10]3[O:13][C:16]([SH:17])=[N:14][C:9]=3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 145622-Amino-4-phenylphenolHCID 2735045Potassium ethylxanthate

Product 1

HCID 178527758HCID 178527758, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Phenyl-2-aminophenol, 11.4 mmol (2.10 g) was dissolved in ethanol, 30 ml, and added potassium ethyl xanthate, 11.4 mmol (1.82 g). The reaction mixture was refluxed overnight, cooled, and excess of ethanol was distilled off, then the reaction mixture was poured into crushed ice. The pH was adjusted to 5 by the addition of acetic acid. The white precipitate formed was filtered and dried to give the crude 5-phenylbenzo[d]oxazole-2-thiol, 2.32 g (90%) that was directly used in the next step without any purification.

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. temperaturecooled
  3. distillationexcess of ethanol was distilled off
  4. additionthe reaction mixture was poured
  5. custominto crushed ice
  6. additionThe pH was adjusted to 5 by the addition of acetic acid
  7. customThe white precipitate formed
  8. filtrationwas filtered
  9. customdried

Sources & evidence

ORD record
ord-5a12a18448524a8ab673279e2e0e8355
Source dataset
uspto-grants-2013_05
Patent number
US08440705B2

Reaction notes

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