Mci-186 → 1-Phenyl-3-methyl-4-(3,4-dichlorophenylcarbamoyl)-2-pyrazolin-5-one

HRID 1706355Notes

Reaction equation

HRID 1706355 reaction equation
[C:1]1([N:7]2[C:11](=[O:12])[CH2:10][C:9]([CH3:13])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:21][C:22]1[CH:23]=[C:24]([N:29]=[C:30]=[O:31])[CH:25]=[CH:26][C:27]=1[Cl:28].C([NH+](CC)CC)C>C1C=CC=CC=1>[C:1]1([N:7]2[C:11](=[O:12])[CH:10]([C:30](=[O:31])[NH:29][C:24]3[CH:25]=[CH:26][C:27]([Cl:28])=[C:22]([Cl:21])[CH:23]=3)[C:9]([CH3:13])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 4021Mci-186HCID 76073,4-Dichlorophenyl isocyanateHCID 8471TriethylamineHCID 1385867Triethylammonium

Product 1

HCID 203354391-Phenyl-3-methyl-4-(3,4-dichlorophenylcarbamoyl)-2-pyrazolin-5-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

The solution of 13 g of 1-phenyl-3-methyl-2-pyrazolin-5-one in 150 ml of benzene and 9.1 g of triethylamine is combined at ambient temperature with the solution of 14.0 g of 3,4-dichlorophenylisocyanate in the minimum amount of benzene. The triethylammonium salt separates after 2 hours standing at room temperature and the mixture is evaporated. The residue is poured into 0.3 N hydrochloric acid, the solid collected, washed with water, dried, triturated with cold methanol and recrystallized from ethyl acetate to yield the 1-phenyl-3-methyl-4-(3,4-dichlorophenylcarbamoyl)-2-pyrazolin-5-one of Formula II with R=H, R'=3--Cl and R"=Cl, melting at 228°-231° (dec.).

Workup

  1. customstanding at room temperature
  2. customthe mixture is evaporated
  3. additionThe residue is poured into 0.3 N hydrochloric acid
  4. customthe solid collected
  5. washwashed with water
  6. customdried
  7. customtriturated with cold methanol
  8. customrecrystallized from ethyl acetate

Sources & evidence

ORD record
ord-4bdbca9fc0164fb2956e6412e6ca482b
Source dataset
uspto-grants-1980_06
Patent number
US04207317

Reaction notes

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