N-(3-Methylphenyl)urea → o-Tolyl Urea Styrene

HRID 1757249Notes

Reaction equation

HRID 1757249 reaction equation
[C:1]1(C)[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]([NH2:10])=[O:9])[CH:2]=1.N[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[CH2:18])=[CH:15][CH:14]=1.[C:21]1(C)C=CC=C(N=C=O)C=1>C(Cl)(Cl)Cl>[CH2:18]=[CH:17][C:16]1[CH:19]=[CH:20][CH:13]=[CH:14][CH:15]=1.[C:2]1([CH3:21])[CH:1]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:7][C:8]([NH2:10])=[O:9]

Participants

5

Reactant 3

HCID 6142N-(3-Methylphenyl)ureaHCID 69303m-Tolyl isocyanateHCID 737004-Aminostyrene

Product 1

HCID 19390271o-Tolyl Urea Styrene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

m-Tolyl Urea Styrerie: 1.00 g (8.40 mmol) of p-aminostyrene (99% Tokyo Kasei) was added to a 250 ml round bottom flask containing 10 ml of chloroform. After ten minutes of mixing, 1.12 g (8.41 mmol) of m-tolyl isocyanate (99% Aldrich) was added dropwise. Within seconds, a white, pinkish precipitate formed. Chloroform (20 ml) was added to aid stirring. The precipitate was filtered to remove the reaction liquid, then washed with 20 ml of chloroform resulting in a white powder (166 g, 78% crude yield, mp=203° C.).

Workup

  1. additionAfter ten minutes of mixing
  2. waitWithin seconds
  3. customa white, pinkish precipitate formed
  4. filtrationThe precipitate was filtered
  5. customto remove
  6. customthe reaction liquid
  7. washwashed with 20 ml of chloroform resulting in a white powder (166 g, 78% crude yield, mp=203° C.)

Sources & evidence

ORD record
ord-5caca81e78bf4c269d78b96110a05180
Source dataset
uspto-grants-1995_08
Patent number
US05444129

Reaction notes

Loading…