Water → 2-Propenamide, 2-methyl-N-(4-(phenylamino)phenyl)-

HRID 895051

Reaction equation

HRID 895051 reaction equation
[NH:1]([C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:20])[C:16](O)([CH3:18])[CH3:17])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>S(=O)(=O)(O)O>[NH:1]([C:8]1[CH:9]=[CH:10][C:11]([NH:14][C:15](=[O:20])[C:16]([CH3:18])=[CH2:17])=[CH:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 962Water2×HCID 20574123N-(4-anilinophenyl)-2-hydroxyisobutyramide

Product 1

HCID 1624682-Propenamide, 2-methyl-N-(4-(phenylamino)phenyl)-Yield 81%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4.85 Grams (0.018 moles) N-(4-anilinophenyl)-2-hydroxyisobutyramide from Example 3 was dissolved in 43.6 grams concentrated sulfuric acid at room temperature in a large test tube. The test tube was then placed in a boiling water bath for 18 minutes before being rapidly cooled in a stream of cold water. This reaction solution was then added dropwise to 800 milliliters of stirred cold water over a 45 minute period. The light green product was filtered off, washed with water and dried in the air to give 3.66 grams N-(4-anilinophenyl)methacrylamide (81% yield). Analysis showed a purity of 92.1%.

Workup

  1. filtrationThe light green product was filtered off
  2. washwashed with water
  3. customdried in the air

Sources & evidence

ORD record
ord-4c833d95a263433d80378a11acd69117
Source dataset
uspto-grants-1981_08
Patent number
US04286105

Linked notes

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