Acetic Acid → 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-methylamino-4-trifluoromethylsulfonylpyrazole

HRID 987073Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 987073
[C:1]([C:3]1[C:7]([S:8]([C:10]([F:13])([F:12])[F:11])=[O:9])=[C:6]([N:14]=[CH:15]OCC)[N:5]([C:19]2[C:24]([Cl:25])=[CH:23][C:22]([C:26]([F:29])([F:28])[F:27])=[CH:21][C:20]=2[Cl:30])[N:4]=1)#[N:2].[BH4-].[Na+].C(O)(=[O:35])C>C(O)C>[C:1]([C:3]1[C:7]([S:8]([C:10]([F:12])([F:13])[F:11])(=[O:35])=[O:9])=[C:6]([NH:14][CH3:15])[N:5]([C:19]2[C:24]([Cl:25])=[CH:23][C:22]([C:26]([F:29])([F:28])[F:27])=[CH:21][C:20]=2[Cl:30])[N:4]=1)#[N:2]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 4311764Sodium borohydride2×HCID 572956413-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxymethylideneamino-4-trifluoromethylsulfinylpyrazole

Produkt 1

HCID 229883203-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-methylamino-4-trifluoromethylsulfonylpyrazoleAusbeute 22,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

A 50 L reactor was charged with 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxymethylideneamino-4-trifluoromethylsulfinylpyrazole (1.645 g, 3.335 moles) and absolute ethanol (16 L) under nitrogen. The solution was cooled to 10° C., and sodium borohydride (266 g, 7.03 moles) was added slowly such that the temperature remained generally below 35° C. After 6.75 h, some additional sodium borohydride (25 g, 0.66 mole) was added and stirring was continued overnight. Acetic acid (1.3 L, 22.7 moles) was added to quench, followed by 16 L of water. The resulting precipitate was collected by filtration, washed with water, and air-dried. Recrystallization from methanol afforded 3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-methylamino-4-trifluoromethylsulfonylpyrazole (350 g) as an off-white solid (m.p. about 227° C.).

Aufarbeitung

  1. customremained generally below 35° C
  2. waitwas continued overnight
  3. customto quench
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water
  6. customair-dried
  7. customRecrystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-0c0a6119baaf48b08780ade78c6993a1
Quelldatensatz
uspto-grants-2003_10
Patentnummer
US06630499B1

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