Carbon Dioxide → HCID 13127600, compound

HRID 1462139Notes

Reaction equation

HRID 1462139 reaction equation
[Na].[C:2]([C:4]1[CH:5]=[N:6][N:7]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[C:29]=2[Cl:36])[C:8]=1[N:9](C(OC1C=CC=CC=1)=O)[C:10]([O:12][C:13]1[CH:18]=CC=C[CH:14]=1)=[O:11])#[N:3].[C:37](=O)=O>C(O)(C)(C)C>[C:13]([O:12][C:10]([NH:9][C:8]1[N:7]([C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[C:30]([Cl:35])[C:29]=2[Cl:36])[N:6]=[CH:5][C:4]=1[C:2]#[N:3])=[O:11])([CH3:37])([CH3:18])[CH3:14]

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 5360545SodiumHCID 13127534HCID 13127534, compound

Product 1

HCID 13127600HCID 13127600, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

Sodium (0.5 g) was added to a stirred mixture of 4-cyano-5-di(phenoxycarbonyl)amino-1-(2,3,4-trichlorophenyl)pyrazole (prepared as described in Example 27; 25 g) in t-butanol (400 ml) and the mixture was heated at reflux for 15 minutes. Solid carbon dioxide pellets were then added to the cooled reaction mixture to adjust the pH to 7. The neutralized reaction mixture was filtered and the filtrate evaporated under reduced pressure to give an oil which was crystallised from ethyl acetate-n-hexane to give 5-t-butoxycarbonylamino-4-cyano-1-(2,3,4-trichlorophenyl)pyrazole (11.0 g), m.p. 140°-141° C., in the form of colourless crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 15 minutes
  3. filtrationThe neutralized reaction mixture was filtered
  4. customthe filtrate evaporated under reduced pressure
  5. customto give an oil which
  6. customwas crystallised from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-f0db08b94aca4374a971c0044c8ed3de
Source dataset
uspto-grants-1984_07
Patent number
US04459150

Reaction notes

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