Trimethyl orthoformate → HCID 54467348, compound

HRID 2253778Notes

Reaction equation

HRID 2253778 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[C:12]([Cl:13])=[CH:11][C:10]([C:14]([F:17])([F:16])[F:15])=[CH:9][C:8]=2[Cl:18])[N:5]=[C:4]([CH3:19])[C:3]=1[C:20]#[N:21].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:34][O:35][CH:36](OC)OC>>[C:20]([C:3]1[C:4]([CH3:19])=[N:5][N:6]([C:7]2[C:8]([Cl:18])=[CH:9][C:10]([C:14]([F:16])([F:15])[F:17])=[CH:11][C:12]=2[Cl:13])[C:2]=1[N:1]=[CH:34][O:35][CH3:36])#[N:21]

Participants

4

Reactant 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 10131783HCID 10131783, compound

Product 1

HCID 54467348HCID 54467348, compound

Procedure

A mixture of 5-amino-4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methylpyrazole (5 g) and p-toluenesulphonic acid hydrate (0.1 g) in trimethylorthoformate (20 ml) was heated at reflux for 4.5 hours. After cooling, the reaction mixture was evaporated to dryness in vacuo. The residue was dissolved in diethyl ether and left to crystallize at 0° C. The dark colored solid was recrystallized from a mixture of ethanol and water to give 4-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-3-methyl-5-methoxymethyleneaminopyrazole (4.67 g), m.p. 75°-78° C., in the form of buff crystals.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4.5 hours
  3. temperatureAfter cooling
  4. customthe reaction mixture was evaporated to dryness in vacuo
  5. dissolutionThe residue was dissolved in diethyl ether
  6. waitleft
  7. customto crystallize at 0° C
  8. customThe dark colored solid was recrystallized from a mixture of ethanol and water

Sources & evidence

ORD record
ord-4e4124d3fa814813aa0985fbac3b3d42
Source dataset
uspto-grants-1993_08
Patent number
US05232940

Reaction notes

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