3-Methyl-2-buten-1-OL → HCID 13118713, compound

HRID 2418123Notes

Reaction equation

HRID 2418123 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=2[Cl:15])[N:5]=[CH:4][C:3]=1[C:16]([O:18][CH3:19])=[O:17].[CH3:20][C:21]([CH3:25])=[CH:22]CO.C[O-].[Na+]>>[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([Cl:14])=[CH:9][C:8]=2[Cl:15])[N:5]=[CH:4][C:3]=1[C:16]([O:18][CH2:19][CH:20]=[C:21]([CH3:25])[CH3:22])=[O:17]

Participants

4

Reactant 3

HCID 111733-Methyl-2-buten-1-OLHCID 10942334Sodium MethoxideHCID 13050480HCID 13050480, compound

Product 1

HCID 13118713HCID 13118713, compound

Procedure

12.0 parts by weight of methyl 5-amino-1-(2,4,6-trichlorophenyl)-pyrazole-4-carboxylate, 24.0 parts by weight of 3-methylbut-2-enol and 0.5 parts by weight of sodium methylate were refluxed for 2 hours (complete conversion), while dry nitrogen was passed over. The excess alcohol was removed under a reduced pressure of from 0.5 to 1.0 mbar/50° C., and the residue was dissolved in 100 ml of ether and precipitated with dry hydrogen chloride gas. The hydrochloride was filtered off with suction and stirred with saturated sodium bicarbonate solution, and the precipitate was filtered off with suction and dried under reduced pressure at 50° C. to give 10.6 g of 3-methylbut-2-enyl 5-amino-1-(2,4,6-trichlorophenyl)-pyrazole-4-carboxylate of melting point 102°-105° C. (active ingredient No.10).

Workup

  1. customThe excess alcohol was removed under a reduced pressure of from 0.5 to 1.0 mbar/50° C.
  2. dissolutionthe residue was dissolved in 100 ml of ether
  3. customprecipitated with dry hydrogen chloride gas
  4. filtrationThe hydrochloride was filtered off with suction
  5. filtrationthe precipitate was filtered off with suction
  6. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-975cfeff92c84852825a5f8b880e6b1f
Source dataset
uspto-grants-1984_09
Patent number
US04472192

Reaction notes

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