O-Xylene → N-(4-anilinophenyl)-2-hydroxyisobutyramide

HRID 895049Notes

Reaction equation

HRID 895049 reaction equation
[OH:1][C:2]([CH3:7])([CH3:6])[C:3](O)=[O:4].[CH:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)=[CH:10][CH:9]=1.C1(C)C(C)=CC=CC=1>C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[NH:14]([C:15]1[CH:16]=[CH:17][C:18]([NH:21][C:3](=[O:4])[C:2]([OH:1])([CH3:7])[CH3:6])=[CH:19][CH:20]=1)[C:11]1[CH:12]=[CH:13][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 7237O-XyleneHCID 7564N-Phenyl-p-phenylenediamineHCID 116712-Hydroxyisobutyric acid

Product 1

HCID 20574123N-(4-anilinophenyl)-2-hydroxyisobutyramideYield 772.4%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 962WaterSolvent2×

Procedure

A 500 milliliter resin pot was charged with 52 grams (0.05 moles) of α-hydroxy isobutyric acid from Example 1, 77.3 grams (0.42 moles) p-aminodiphenylamine, 1 gram p-toluene sulfonic acid and 140 mls. of xylene under a nitrogen blanket. A Dean-Stark water separator and a condenser was attached to the resin pot and the mixture was heated to vigorous reflux with H2O being removed as it was formed. After 3 hours of reflux the heat was removed and the product was allowed to crystallize in the resin pot under nitrogen. The product was broken up, washed with toluene, filtered and dried to obtain 104.4 grams (92% yield) of N-(4-anilinophenyl)-2-hydroxyisobutyramide with a melting point of 171°-174° C.

Workup

  1. temperaturethe mixture was heated
  2. customremoved as it
  3. customwas formed
  4. temperatureAfter 3 hours of reflux the heat
  5. customwas removed
  6. customto crystallize in the resin pot under nitrogen
  7. washwashed with toluene
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-4b45ce61eec4486ea8736456888811ec
Source dataset
uspto-grants-1981_08
Patent number
US04286105

Reaction notes

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