Mci-186 → Triethylammonium salt-methanolate

HRID 1706356

Reaction equation

HRID 1706356 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.[CH2:14]([N:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[CH3:15].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][C:23]=1[N:29]=[C:30]=[O:31]>C1C=CC=CC=1>[CH3:11][O-:12].[CH2:14]([NH+:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[CH3:15].[C:1]1([N:7]2[C:11](=[O:12])[CH:10]([C:30](=[O:31])[NH:29][C:23]3[CH:24]=[C:25]([Cl:28])[CH:26]=[CH:27][C:22]=3[Cl:21])[C:9]([CH3:13])=[N:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 4021Mci-186HCID 8471TriethylamineHCID 79360Benzene, 1,4-dichloro-2-isocyanato-

Product 2

HCID 19855321Triethylammonium salt-methanolateHCID 203354281-Phenyl-3-methyl-4-(2,5-dichlorophenylcarbamoyl)-2-pyrazolin-5-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

The solution of 4.7 g of 1-phenyl-3-methyl-2-pyrazolin-5-one in 75 ml of benzene and 3.3 g of triethylamine is combined with the solution of 5.1 g of 2,5-dichlorophenylisocyanate in 25 ml of benzene. After warming the mixture briefly on the steam cone, the resulting solution is allowed to stand for 2 hours at room temperature. It is evaporated, the residue triturated with diethyl ether and recrystallized from methanol-diethyl ether to yield the triethylammonium salt-methanolate of the 1-phenyl-3-methyl-4-(2,5-dichlorophenylcarbamoyl)-2-pyrazolin-5-one, melting at 142°-147°, resolidifying and remelting at 154°-159°.

Workup

  1. temperatureAfter warming the mixture briefly on the steam cone
  2. customIt is evaporated
  3. customthe residue triturated with diethyl ether
  4. customrecrystallized from methanol-diethyl ether

Sources & evidence

ORD record
ord-49370d02af14492aa1a4cb74d165d926
Source dataset
uspto-grants-1980_06
Patent number
US04207317

Linked notes

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