Trimethyl orthoformate → HCID 54467348, compound

HRID 975515Notes

Reaction equation

HRID 975515 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-a7003f38d5234d0b88953b46cadfa64f
Source dataset
uspto-grants-1997_03
Patent number
US05608077

Reaction notes

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