3,4-Dichlorophenyl isocyanate → HCID 20335432, compound

HRID 1706360Notes

Reaction equation

HRID 1706360 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13](=[O:14])[CH2:12][C:11]([CH3:15])=[N:10]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[Cl:23][C:24]1[CH:25]=[C:26]([N:31]=[C:32]=[O:33])[CH:27]=[CH:28][C:29]=1[Cl:30]>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13](=[O:14])[CH:12]([C:32](=[O:33])[NH:31][C:26]3[CH:27]=[CH:28][C:29]([Cl:30])=[C:24]([Cl:23])[CH:25]=3)[C:11]([CH3:15])=[N:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 76073,4-Dichlorophenyl isocyanateHCID 8471TriethylamineHCID 1247322-(4-Methoxyphenyl)-5-methyl-2,4-dihydro-3H-pyrazol-3-one

Product 1

HCID 20335432HCID 20335432, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

The stirred solution of 4.1 g of 1-(p-methoxyphenyl)-3-methyl-2-pyrazolin-5-one in 75 ml of warm benzene and 2.4 g of triethylamine is combined with the solution of 3.8 g of 3,4-dichlorophenylisocyanate in 50 ml of benzene. After standing at ambient temperature for 4 hours, the benzene is evaporated, the residue taken up in methanol and the solution poured into 100 ml of 0.3 N hydrochloric acid. The mixture is allowed to stand overnight at room temperature, the precipitate is collected, washed with water, dried, triturated with benzene-ethyl acetate and recrystallized from methanol to yield the 1-(p-methoxyphenyl)-3-methyl-4-(3,4-dichlorophenylcarbamoyl)-2-pyrazolin-5-one of Formula II with R=OCH3, R'=3--Cl and R"=Cl, melting at 120°-125°, resolidifying and remelting at 228°-232° (dec.).

Workup

  1. customthe benzene is evaporated
  2. additionthe solution poured into 100 ml of 0.3 N hydrochloric acid
  3. waitto stand overnight at room temperature
  4. customthe precipitate is collected
  5. washwashed with water
  6. customdried
  7. customtriturated with benzene-ethyl acetate
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-76218720fce94a4dabcb56925f1b8c9b
Source dataset
uspto-grants-1980_06
Patent number
US04207317

Reaction notes

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