HCID 3017661, compound → N,N'-Diphenyloxamide

HRID 991021Notes

Reaction equation

HRID 991021 reaction equation
[C:1]([O-:6])(=O)[C:2]([NH2:4])=[O:3].[NH2:7][C:8]1[CH:13]=[CH:12][C:11](C(C2C=CC(O)=CC=2)(C)C)=[CH:10][CH:9]=1>ClC1C=CC=CC=1Cl>[CH:11]1[CH:12]=[CH:13][C:8]([NH:7][C:1]([C:2]([NH:4][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:3])=[O:6])=[CH:9][CH:10]=1

Participants

4

Reactant 2

HCID 3017661HCID 3017661, compoundHCID 11148864Phenol, 4-[1-(4-aminophenyl)-1-methylethyl]-

Product 1

HCID 69288N,N'-Diphenyloxamide

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

Ar=2,2-(4,4′-phenylene)propyl (also known as compound (VIII)): A mixture of oxamate, compound (XII), (2.415 g, 10.18 mmol) and 2-(4-aminophenyl)-2-(4′-hydroxyphenyl)propane (2.545 g, 11.2 mmol) were suspended in o-dichlorobenzene (10 ml), degassed, and heated to reflux for 20 hrs. TLC indicated complete conversion of the oxamate. The crude reaction mixture was concentrated under reduced pressure, taken up in dichloromethane, and filtered through a plug of silica gel. The product was recrystallized from hexanes/dichloromethane and again filtered through silica gel, yielding the desired oxanilide as white fine crystals.

Workup

  1. customdegassed
  2. temperatureheated
  3. temperatureto reflux for 20 hrs
  4. customThe crude reaction mixture
  5. concentrationwas concentrated under reduced pressure
  6. filtrationfiltered through a plug of silica gel
  7. customThe product was recrystallized from hexanes/dichloromethane
  8. filtrationagain filtered through silica gel

Sources & evidence

ORD record
ord-ada3744472f5433785a31df7ec55bf31
Source dataset
uspto-grants-2002_10
Patent number
US06462168B1

Reaction notes

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