2,6-Dichlorobenzoyl isocyanate → 1-(2,6-Dichlorobenzoyl)-3-(5-methyl-6-phenyl-3-pyridyl)urea

HRID 1980331Notes

Reaction equation

HRID 1980331 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([NH2:14])[CH:5]=[N:6][C:7]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Cl:15][C:16]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:17]=1[C:18]([N:20]=[C:21]=[O:22])=[O:19]>C(#N)C>[Cl:15][C:16]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[C:17]=1[C:18]([NH:20][C:21]([NH:14][C:4]1[CH:5]=[N:6][C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:2]([CH3:1])[CH:3]=1)=[O:22])=[O:19]

Participants

4

Reactant 2

HCID 129127392,6-Dichlorobenzoyl isocyanateHCID 135028615-Methyl-6-phenylpyridin-3-amine

Product 1

HCID 132427361-(2,6-Dichlorobenzoyl)-3-(5-methyl-6-phenyl-3-pyridyl)urea

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5-Methyl-6-phenyl-3-pyridylamine (0.4 gram) in 20 ml of acetonitrile was added to 2,6-dichlorobenzoyl isocyanate (0.5 gram) under nitrogen and at room temperature. After about 10-20 minutes a precipitate formed. The reaction mixture was then stirred for about 4-5 hours and the product was filtered and washed with acetonitrile, yield, 580 mg, m.p. 202°-205° C. A small portion of the product was recrystallized from ethanol, m.p. 204°-209° C.

Workup

  1. customAfter about 10-20 minutes a precipitate formed
  2. filtrationthe product was filtered
  3. washwashed with acetonitrile
  4. customyield
  5. customA small portion of the product was recrystallized from ethanol, m.p. 204°-209° C.

Sources & evidence

ORD record
ord-97bacf270ac041e983bd9dee689f856a
Source dataset
uspto-grants-1985_04
Patent number
US04508722

Reaction notes

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