2-Tolyl isocyanate → o-Tolyl Urea Styrene

HRID 1609682Notes

Reaction equation

HRID 1609682 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[CH2:7])=[CH:4][CH:3]=1.[C:10]1([CH3:19])[C:11]([N:16]=[C:17]=[O:18])=[CH:12][CH:13]=[CH:14][CH:15]=1>C(Cl)(Cl)Cl>[CH2:7]=[CH:6][C:5]1[CH:8]=[CH:9][CH:2]=[CH:3][CH:4]=1.[C:10]1([CH3:19])[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[NH:16][C:17]([NH2:1])=[O:18]

Participants

4

Reactant 2

HCID 691942-Tolyl isocyanateHCID 737004-Aminostyrene

Product 1

HCID 19390271o-Tolyl Urea Styrene

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

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 o-tolyl isocyanate (99% Aldrich) was added dropwise. Within seconds, a yellow precipitate formed. The precipitate was filtered to remove the reaction liquid, then washed with 20 ml of chloroform resulting in pale yellow powder (1.45 g, 68% crude yield, mp=193° C.).

Workup

  1. additionAfter ten minutes of mixing
  2. waitWithin seconds
  3. customa yellow precipitate formed
  4. filtrationThe precipitate was filtered
  5. customto remove
  6. customthe reaction liquid
  7. washwashed with 20 ml of chloroform resulting in pale yellow powder (1.45 g, 68% crude yield, mp=193° C.)

Sources & evidence

ORD record
ord-7e32ce71c73e487bb45769959123f0b9
Source dataset
uspto-grants-1995_03
Patent number
US05401825

Reaction notes

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