Trimethyl orthoformate → 5-amino-1-[2,6-dichloro4-(trifluoromethyl)phenyl]-3-[(1,1-dimethoxy)ethyl]4-methylthio-1H-pyrazole

HRID 1106686Notes

Reaction equation

HRID 1106686 reaction equation
[C:1]([C:4]1[C:8]([S:9][CH3:10])=[C:7]([NH2:11])[N:6]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:22])([F:21])[F:20])=[CH:14][C:13]=2[Cl:23])[N:5]=1)(=[O:3])[CH3:2].[CH:24](OC)(OC)[O:25]C.O.[C:32]1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CO>[NH2:11][C:7]1[N:6]([C:12]2[C:17]([Cl:18])=[CH:16][C:15]([C:19]([F:20])([F:21])[F:22])=[CH:14][C:13]=2[Cl:23])[N:5]=[C:4]([C:1]([O:25][CH3:24])([O:3][CH3:32])[CH3:2])[C:8]=1[S:9][CH3:10]

Participants

6

Reactant 4

HCID 9005Trimethyl orthoformateHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 117839363-acetyl-5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylthio-1H-pyrazole

Product 1

HCID 110590595-amino-1-[2,6-dichloro4-(trifluoromethyl)phenyl]-3-[(1,1-dimethoxy)ethyl]4-methylthio-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 2.0 g (0.0052 mole) of 3-acetyl-5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-methylthio-1H-pyrazole, 1.7 ml (0.0156 mole) of trimethyl orthoformate, 0.060 g (0.0003 mole) of para-toluenesulfonic acid monohydrate and 10 ml of methanol was heated at 40° C. for about 8 hours, then left 64 h at 20° C. The mixture was mixed with a saturated solution of NaHCO3, extracted with dichloromethane, and successively dried, filtered, evaporated, chromatographed on silica gel. 0.59 g of the title compound having a melting point of about 149° C. was obtained.

Workup

  1. extractionextracted with dichloromethane
  2. customsuccessively dried
  3. filtrationfiltered
  4. customevaporated
  5. customchromatographed on silica gel
  6. customwas obtained

Sources & evidence

ORD record
ord-fe81818adb91492a9bc1a9e1bd7ff4f6
Source dataset
uspto-grants-2000_05
Patent number
US06057354

Reaction notes

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