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

HRID 498133Notes

Reaction equation

HRID 498133 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 92%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

Diketene (18.6 g, 0.221 mol) was added dropwise at 60° C. to a solution of N-phenyl-p-phenylenediamine (40.00 g, 0.217 mol) in 40% strength acetic acid (100.00 g) in the course of 40 min. The reaction mixture was stirred at 65° C. for 30 min and cooled to 15° C. The very viscous suspension was filtered. The precipitate was washed with 40% strength acetic acid (2×25 g) and water (2×25 g) and dried at 50° C. in vacuo (20 mbar). 53.50 g (92% yield) of 3-oxo-N-[4-(phenylamino)phenyl]butyramide were obtained as a light grey solid. Mp: 93.0° C.

Workup

  1. temperaturecooled to 15° C
  2. filtrationThe very viscous suspension was filtered
  3. washThe precipitate was washed with 40% strength acetic acid (2×25 g) and water (2×25 g)
  4. customdried at 50° C. in vacuo (20 mbar)

Sources & evidence

ORD record
ord-347ef9beabf34d5eabe81c57cf4c74b0
Source dataset
uspto-grants-2005_09
Patent number
US06949677B2

Reaction notes

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