4-Aminophenol → 1,2-Benzisoselenazol-3(2H)-one, 2-(4-hydroxyphenyl)-

HRID 1649535Notes

Reaction equation

HRID 1649535 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:16]1C=CC=C[C:17]=1[C:18](Cl)=[Se:19].[O:25]1[CH2:29][CH2:28][CH2:27][CH2:26]1>>[OH:8][C:5]1[CH:6]=[CH:7][C:2]([N:1]2[C:29](=[O:25])[C:28]3[CH:27]=[CH:26][CH:16]=[CH:17][C:18]=3[Se:19]2)=[CH:3][CH:4]=1

Participants

5

Reactant 4

HCID 4034-AminophenolHCID 1049PyridineHCID 8028Tetrahydrofuran2×HCID 22643532HCID 22643532, compound

Product 1

HCID 30675781,2-Benzisoselenazol-3(2H)-one, 2-(4-hydroxyphenyl)-

Procedure

of 4-aminophenol dissolved in 200 cc. of tetrahydrofurane (THF) and 2 cc. of pyridine are added with stirring and ice-cooling (temperature below 10° C.) under a nitrogen atmosphere to a solution of 3.3 g. of o-chloroselenobenzoic acid chloride in 30 cc. of THF. After termination of the addition, the mixture is stirred at room temperatur, the solvent is evaporated under vacuum and the residue is pured into a mixture of ice and dilute hydrochloric acid. The resulting precipitate is filtered off and is recrystallized from ethanol.

Workup

  1. temperatureice-cooling (temperature below 10° C.) under a nitrogen atmosphere to a solution of 3.3 g
  2. additionAfter termination of the addition
  3. stirringthe mixture is stirred at room temperatur
  4. customthe solvent is evaporated under vacuum
  5. additionthe residue is pured into a mixture of ice and dilute hydrochloric acid
  6. filtrationThe resulting precipitate is filtered off
  7. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-3996c9aad54b4c5697d6d3e18db36d1d
Source dataset
uspto-grants-1983_11
Patent number
US04418069

Reaction notes

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