Trimethyl orthoformate → HCID 54467348, compound

HRID 1078450Notes

Reaction equation

HRID 1078450 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-e2f85160b1cf4d8ba43f347b7870c3e8
Source dataset
uspto-grants-1996_08
Patent number
US05547974

Reaction notes

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