Carbon Dioxide → HCID 13127601, compound

HRID 1462140Notes

Reaction equation

HRID 1462140 reaction equation
C(OCC=C)C=C.[Na].[C:9]([C:11]1[CH:12]=[N:13][N:14]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([Cl:42])[C:36]=2[Cl:43])[C:15]=1[N:16](C(OC1C=CC=CC=1)=O)[C:17]([O:19][C:20]1C=CC=[CH:22][CH:21]=1)=[O:18])#[N:10].C(=O)=O>C(O)C=C.O1CCCC1>[C:9]([C:11]1[CH:12]=[N:13][N:14]([C:35]2[CH:40]=[CH:39][C:38]([Cl:41])=[C:37]([Cl:42])[C:36]=2[Cl:43])[C:15]=1[NH:16][C:17]([O:19][CH2:20][CH:21]=[CH2:22])=[O:18])#[N:10]

Participants

6

Reactant 3

HCID 280Carbon DioxideHCID 13127534HCID 13127534, compoundHCID 86738583HCID 86738583, compound

Product 1

HCID 13127601HCID 13127601, compound

Reagents, catalysts & solvents 2

HCID 7858Allyl AlcoholSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of sodium 2-propenyloxide in allyl alcohol [30 ml; prepared by dissolving sodium metal (1.0 g) in allyl alcohol (40 ml)] was added to a stirred solution of 4-cyano-5-di(phenoxycarbonyl)amino-1-(2,3,4-trichlorophenyl)pyrazole (15 g) in tetrahydrofuran (300 ml). The mixture was stirred for 15 minutes at laboratory temperature then solid carbon dioxide pellets added to adjust the pH of the solution to pH7. The neutralized solution was filtered through diatomaceous earth and then evaporated under reduced pressure and the residue crystallised from a mixture of ethyl acetate and hexane to give 4-cyano-5-(2-propenyloxycarbonylamino)-1-(2,3,4-trichlorophenyl)pyrazole, m.p. 154°-155° C., in the form of colourless crystals.

Workup

  1. filtrationThe neutralized solution was filtered through diatomaceous earth
  2. customevaporated under reduced pressure
  3. customthe residue crystallised from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-13a4a4e6ded6420cbcf2aeab00c26831
Source dataset
uspto-grants-1984_07
Patent number
US04459150

Reaction notes

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