HCID 20395011, compound → HCID 20395014, compound

HRID 261409Notes

Reaction equation

HRID 261409 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([C:8]([C:10]2[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:13]([OH:20])=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:11]=2)=[O:9])=[CH:6][CH:5]=1)([O-])=O.[NH4+]=S>C(O)C>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:8]([C:10]2[CH:15]=[C:14]([C:16]([CH3:18])([CH3:19])[CH3:17])[C:13]([OH:20])=[C:12]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:11]=2)=[O:9])=[CH:25][CH:26]=1

Participants

3

Reactant 1

HCID 20395011HCID 20395011, compound

Product 1

HCID 20395014HCID 20395014, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5 g. of 4-(4-nitrobenzoyl)-2,6-di(t-butyl)phenol in 150 ml. of ethanol is treated with 40 ml. of ammonium sulfide solution. The mixture is heated at reflux for 2 hours then stirred without heating for about 16 hours. An additional 40 ml. of ammonium sulfide solution is added, and the mixture is heated at reflux for 4 hours more. After an additional 16 hours without heating, the mixture is extracted with dichloromethane, and the extracts are dried. Evaporation of the dried extracts provides a solid residue which is recrystallized twice from a benzene-hexane mixture to provide 4-(4-aminobenzoyl)-2,6-di(t-butyl)phenol as a light yellow solid, m.p. 164.5°-166.5° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 2 hours
  3. temperaturewithout heating for about 16 hours
  4. temperaturethe mixture is heated
  5. temperatureat reflux for 4 hours more
  6. temperatureAfter an additional 16 hours without heating
  7. extractionthe mixture is extracted with dichloromethane
  8. customthe extracts are dried
  9. customEvaporation of the dried extracts
  10. customprovides a solid residue which
  11. customis recrystallized twice from a benzene-hexane mixture

Sources & evidence

ORD record
ord-dae0cd0abf324f229c6c95b23df1c408
Source dataset
uspto-grants-1979_08
Patent number
US04165383

Reaction notes

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