Trimethyl orthoformate → HCID 54467348, compound

HRID 842154Notes

Reaction equation

HRID 842154 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-ef869e4fe07f4a7da0a844b9eb313941
Source dataset
uspto-grants-2002_04
Patent number
US06372774B1

Reaction notes

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