2-Aminophenol → HCID 20060589, compound

HRID 1723424Notes

Reaction equation

HRID 1723424 reaction equation
[N:1]([CH:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5]1)=[C:2]=S.[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[OH:21].[S]>[Hg]=O.C(#N)C>[O:21]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]=[C:2]1[NH:1][CH:4]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5]1

Participants

6

Reactant 3

HCID 58012-AminophenolHCID 5362487SulfurHCID 14575268Ethyl 3-isothiocyanatopyrrolidine-1-carboxylate

Product 1

HCID 20060589HCID 20060589, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 55 parts of ethyl 3-isothiocyanato-1-pyrrolidinecarboxylate, 23.6 parts of 2-aminophenol and 320 parts of acetonitrile was stirred and refluxed for 4 hours. Then there were added 93 parts of mercury(II) oxide and 0.5 parts of sulfur while stirring vigorously. The reaction mixture was stirred and refluxed overnight. After cooling, the mixture was filtered over diatomaceous earth and the filtrate was evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (99:1 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 38 parts (64%) of ethyl 3-[(2-benzoxazolyl)amino]-1-pyrrolidinecarboxylate as a residue (38).

Workup

  1. temperaturerefluxed for 4 hours
  2. stirringwhile stirring vigorously
  3. stirringThe reaction mixture was stirred
  4. temperaturerefluxed overnight
  5. temperatureAfter cooling
  6. filtrationthe mixture was filtered over diatomaceous earth
  7. customthe filtrate was evaporated
  8. customThe residue was purified by column chromatography over silica gel using
  9. additiona mixture of trichloromethane and methanol (99:1 by volume) as eluent
  10. customThe pure fractions were collected
  11. customthe eluent was evaporated

Sources & evidence

ORD record
ord-cd27af03d44449eabde5d1dac4692308
Source dataset
uspto-grants-1989_08
Patent number
US04861785

Reaction notes

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