Water → HCID 13127534, compound

HRID 1462135Notes

Reaction equation

HRID 1462135 reaction equation
[H-].[Na+].[NH2:3][C:4]1[N:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[C:10]=2[Cl:17])[N:7]=[CH:6][C:5]=1[C:18]#[N:19].Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22].[OH2:30]>CN(C)C=O.C(O)C>[C:18]([C:5]1[CH:6]=[N:7][N:8]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[C:10]=2[Cl:17])[C:4]=1[N:3]([C:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:30])[C:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22])#[N:19]

Participants

7

Reactant 4

HCID 962WaterHCID 15891Phenyl chloroformateHCID 24758Sodium hydrideHCID 30189015-amino-1-(2,3,4-trichlorophenyl)-1H-pyrazole-4-carbonitrile

Product 1

HCID 13127534HCID 13127534, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
10 °C

Procedure

Sodium hydride (0.5 g) was added to a solution of 5-amino-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole (5.8 g) in dimethylformamide (20 ml). After the initial exothermic reaction had subsided, the solution was heated on a steam-bath for 5 minutes and then cooled to 10° C. Phenyl chloroformate (2.8 ml) was then added slowly in small portions with occasional cooling with water to keep the temperature below 50° C. The mixture was then heated on a steam-bath for 10 minutes, cooled and evaporated to dryness. The solid residue was treated with diethyl ether (300 ml). The ethereal suspension was filtered and the filtrate was evaporated to dryness. The solid residue thus obtained was boiled in ethanol (200 ml) and separated by filtration, to give 4-cyano-5-di(phenoxycarbonyl)amino-1-(2,3,4-trichlorophenyl)pyrazole (1.7 g), m.p. 206°-208° C., in the form of colourless crystals.

Workup

  1. customAfter the initial exothermic reaction
  2. temperaturethe solution was heated on a steam-bath for 5 minutes
  3. customthe temperature below 50° C
  4. temperatureThe mixture was then heated on a steam-bath for 10 minutes
  5. temperaturecooled
  6. customevaporated to dryness
  7. additionThe solid residue was treated with diethyl ether (300 ml)
  8. filtrationThe ethereal suspension was filtered
  9. customthe filtrate was evaporated to dryness
  10. customThe solid residue thus obtained
  11. customseparated by filtration

Sources & evidence

ORD record
ord-fec586de0cd14fa38ccab7cab1de342c
Source dataset
uspto-grants-1984_07
Patent number
US04459150

Reaction notes

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