Acetic Acid → 1-(2,6-Dichloro-4-trifluoromethylphenyl)-3-cyano-5-methylamino-4-trifluoromethylsulfinylpyrazole

HRID 1275108노트

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HRID 1275108 반응식
[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)C>C(O)C>[C:1]([C:3]1[C:7]([S:8]([C:10]([F:11])([F:12])[F:13])=[O:9])=[C:6]([NH:14][CH3:15])[N:5]([C:19]2[C:20]([Cl:30])=[CH:21][C:22]([C:26]([F:28])([F:27])[F:29])=[CH:23][C:24]=2[Cl:25])[N:4]=1)#[N:2]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 4311764Sodium borohydride2회HCID 572956413-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-5-ethoxymethylideneamino-4-trifluoromethylsulfinylpyrazole

생성물 1

HCID 114308641-(2,6-Dichloro-4-trifluoromethylphenyl)-3-cyano-5-methylamino-4-trifluoromethylsulfinylpyrazole수율 23.3%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
10 °C

실험 절차

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 moles) 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-trifluoromethylsulfinylpyrazole (350 g) as an off-white solid. (m.p. about 227° C.)

후처리

  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

출처 및 근거

ORD 기록
ord-3266cce3e22f425ab3f67aae0a103a8f
출처 데이터셋
uspto-grants-2000_12
특허 번호
US06160002

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