Ethyl orthoformate → 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxymethylideneamino-4-trifluoromethylsulfinylpyrazole

HRID 987072Notes

Reaction equation

HRID 987072 reaction equation
[CH:1]1[C:2]([C:23]([F:26])([F:25])[F:24])=[CH:3][C:4]([Cl:22])=[C:5]([N:8]2[N:12]=[C:11]([C:13]#[N:14])[C:10]([S+:15]([O-:20])[C:16]([F:19])([F:18])[F:17])=[C:9]2[NH2:21])[C:6]=1[Cl:7].[CH:27](OCC)(OCC)[O:28][CH2:29][CH3:30]>O>[C:13]([C:11]1[C:10]([S:15]([C:16]([F:19])([F:17])[F:18])=[O:20])=[C:9]([N:21]=[CH:27][O:28][CH2:29][CH3:30])[N:8]([C:5]2[C:4]([Cl:22])=[CH:3][C:2]([C:23]([F:24])([F:26])[F:25])=[CH:1][C:6]=2[Cl:7])[N:12]=1)#[N:14]

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 178510672HCID 178510672, compound

Product 1

HCID 572956413-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxymethylideneamino-4-trifluoromethylsulfinylpyrazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 12-L three-necked flask fitted with an overhead stirrer, heating mantle, water separator (e.g. Dean Stark trap) with condenser was placed under a nitrogen atmosphere and charged with 1.475 kg (3.37 moles) of fipronil and 6 L of triethyl orthoformate. The suspension was heated to reflux over 2.5 h, then at reflux for 3 h with collection and removal of the distillate. The mixture was cooled to room temperature, then evaporated under reduced pressure at a bath temperature of 60-80° C., then at 50° C. overnight. The resulting beige solid, 1.717 kg (95.8% by HPLC, 3.335 moles, 99% purity corrected yield) was used without further purification (m.p. about 63° C.).

Workup

  1. customA 12-L three-necked flask fitted with an overhead stirrer
  2. temperatureheating mantle
  3. temperatureThe suspension was heated
  4. temperatureto reflux over 2.5 h
  5. temperatureat reflux for 3 h with collection and removal of the distillate
  6. customevaporated under reduced pressure at a bath temperature of 60-80° C.
  7. customat 50° C.
  8. customovernight
  9. customThe resulting beige solid, 1.717 kg (95.8% by HPLC, 3.335 moles, 99% purity corrected yield)
  10. customwas used without further purification (m.p. about 63° C.)

Sources & evidence

ORD record
ord-7b602385403442f6847cab56d3263530
Source dataset
uspto-grants-2003_10
Patent number
US06630499B1

Reaction notes

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