Dichloromethane → 3-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole

HRID 376226노트

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HRID 376226 반응식
N(OC(C)(C)C)=O.N[C:9]1[N:13]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][C:15]=2[Cl:25])[N:12]=[C:11]([C:26]#[N:27])[C:10]=1[C:28](=[O:33])[C:29]([F:32])([F:31])[F:30].CCCCCC.ClCCl>O1CCCC1>[C:26]([C:11]1[C:10]([C:28](=[O:33])[C:29]([F:30])([F:31])[F:32])=[CH:9][N:13]([C:14]2[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:22])[F:23])=[CH:16][C:15]=2[Cl:25])[N:12]=1)#[N:27]

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 8058HexaneHCID 10906Tert-Butyl nitrite2회HCID 186994595-Amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole

생성물 1

HCID 186994613-Cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
55 °C

실험 절차

t-Butyl nitrite (12.45 ml) was added dropwise to a stirred solution of 5-amino-3-cyano-1-(2,6-dichloro-4-trifluoromethylphenyl)-4-trifluoroacetylpyrazole (JP-A-8-311036; 30 g) in tetrahydrofuran (250 ml) and the mixture stirred at 55° C. for 16 hours. Further quantities of t-butyl nitrite added/subsequent periods of stirring at 55° C. were as follows: 9 ml/7 hours, 6 ml/16 hours, 9 ml/6 hours, 4.75 ml/16 hours, 6 ml/6 hours and 3.5 ml/22 hours. The reaction mixture was allowed to cool and evaporated under reduced pressure, then the residue combined with those obtained from three identical preparations. Purification by column chromatography on silica gel (1 Kg), using hexane:dichloromethane (6:4) and then dichloromethane as eluants, gave a yellow oil which, on trituration with hexane (3×50 ml) followed by dichloromethane (100 ml), provided the title compound as a white solid, m.p. 124-125° C. δ (CDCl3): 7.83 (s,2H), 8.30 (s,1H). MS (thermospray): M/Z [M+H] 401.7; C13H3Cl2F6N3O+H requires 401.96.

후처리

  1. custom9 ml/7 hours, 6 ml/16 hours, 9 ml/6 hours, 4.75 ml/16 hours, 6 ml/6 hours and 3.5 ml/22 hours
  2. temperatureto cool
  3. customevaporated under reduced pressure
  4. customthose obtained from three identical preparations
  5. customPurification by column chromatography on silica gel (1 Kg)
  6. customdichloromethane as eluants, gave a yellow oil which

출처 및 근거

ORD 기록
ord-550e22cc62cf41adbf3188dc5fe10c80
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06019986

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