3-Aminophenol → 3-Amino-4'-(M-Aminophenoxy) Benzophenone

HRID 1494623Notes

Reaction equation

HRID 1494623 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+].[NH2:11][C:12]1[CH:13]=[C:14]([CH:24]=[CH:25][CH:26]=1)[C:15]([C:17]1[CH:22]=[CH:21][C:20](Cl)=[CH:19][CH:18]=1)=[O:16].S([O-])([O-])=O.[Na+].[Na+]>CS(C)=O.C1(C)C=CC=CC=1.O>[NH2:11][C:12]1[CH:13]=[C:14]([CH:24]=[CH:25][CH:26]=1)[C:15]([C:17]1[CH:22]=[CH:21][C:20]([O:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH2:1])[CH:3]=2)=[CH:19][CH:18]=1)=[O:16]

Participants

8

Reactant 4

HCID 115683-AminophenolHCID 14798Sodium Hydroxide2×HCID 24437Sodium SulfiteHCID 13609452(3-Aminophenyl)(4-chlorophenyl)methanone

Product 1

HCID 151767373-Amino-4'-(M-Aminophenoxy) BenzophenoneYield 74.7%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

A solution of m-aminophenol 25 g (0.23 mol.) in 160 ml of dimethylsulfoxide and 190 ml of toluene was degassed for 30 minutes by bubbling nitrogen. The temperature was raised to 50° C. and 9.16 g (0.23 mol) of sodium hydroxide as 50% aqueous solution was added. The reaction temperature was slowly raised to 110° C. (oil bath 140° C.) and water was distilled off via toluene-water azeotrope. After all the water was distilled off, the toluene was distilled off till the reaction temperature reached 160° C. Reaction mixture was cooled to 80° C. and 3-amino-4'-chlorobenzophenone 53 g (0.23 mol) was added in small portions. After the addition was complete the reaction temperature was raised to 150° C. and maintained for 4 hours. After cooling to room temperature, the reaction mixture was poured into 800 ml of 2% sodium hydroxide and 1% sodium sulfite solution with rapid stirring. The precipitate semi-solid obtained was washed with water and then taken up in 200 ml of chloroform. The chloroform solution was washed twice with water. After drying with magnesium sulfate, chloroform was removed to provide a dark yellow resin like solid 52.3 g (72%), m.p. 48°-52° C.

Workup

  1. customby bubbling nitrogen
  2. distillationwas distilled off via toluene-water azeotrope
  3. distillationAfter all the water was distilled off
  4. distillationthe toluene was distilled off till the reaction temperature
  5. customreached 160° C
  6. customReaction mixture
  7. temperaturewas cooled to 80° C.
  8. additionAfter the addition
  9. temperaturewas raised to 150° C.
  10. temperaturemaintained for 4 hours
  11. temperatureAfter cooling to room temperature
  12. customThe precipitate semi-solid obtained
  13. washwas washed with water
  14. washThe chloroform solution was washed twice with water
  15. dry with materialAfter drying with magnesium sulfate, chloroform
  16. customwas removed

Sources & evidence

ORD record
ord-107206e0b6e74a4b8ba7fb26ea221f4a
Source dataset
uspto-grants-1991_06
Patent number
US05026872

Reaction notes

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