N-Phenyl-p-phenylenediamine → HCID 879512, compound

HRID 498132Notes

Reaction equation

HRID 498132 reaction equation
[CH2:1]=[C:2]1[O:6][C:4](=[O:5])[CH2:3]1.[C:7]1([NH:13][C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)(=O)C>[O:6]=[C:2]([CH3:1])[CH2:3][C:4]([NH:20][C:17]1[CH:16]=[CH:15][C:14]([NH:13][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:19][CH:18]=1)=[O:5]

Participants

4

Reactant 2

HCID 7564N-Phenyl-p-phenylenediamineHCID 12661Diketene

Product 1

HCID 879512HCID 879512, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
65 °C

Procedure

Diketene (160.13 g, 1.904 mol) and a solution of N-phenyl-p-phenylenediamine (344.00 g, 1.867 mol) in 40% strength acetic acid (1300.00 g) were simultaneously added dropwise at 60° C. in the course of about 4.5 h to 40% strength acetic acid (300.00 g). After addition of the starting materials had taken place, the reaction mixture was stirred at 65° C. for 30 min and then cooled to 15° C. The resulting precipitate was filtered off on a suction filter, washed with 40% strength acetic acid (2×200 g) and with water (2×200 g) and dried at 50° C. in vacuo (20 mbar). 415.31 g (95.3% content, 79% yield) of 3-oxo-N-[4-(phenylamino)phenyl]butyramide were obtained as a light grey solid. Mp: 89.5° C.;

Workup

  1. additionAfter addition of the starting materials
  2. temperaturecooled to 15° C
  3. filtrationThe resulting precipitate was filtered off on a suction
  4. filtrationfilter
  5. washwashed with 40% strength acetic acid (2×200 g) and with water (2×200 g)
  6. customdried at 50° C. in vacuo (20 mbar)

Sources & evidence

ORD record
ord-5a882f76bed54be3a290828825bdbf45
Source dataset
uspto-grants-2005_09
Patent number
US06949677B2

Reaction notes

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