Water → 2-Cyclobutylmethylthio-4-(3-trifluoromethylpyrazolyl)benzonitrile

HRID 25278

반응식

HRID 25278 반응식
[SH:1][C:2]1[CH:9]=[C:8]([C:10]2[C:11]([C:15]([F:18])([F:17])[F:16])=[N:12][NH:13][CH:14]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH:19]1([CH2:23]Br)[CH2:22][CH2:21][CH2:20]1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:19]1([CH2:23][S:1][C:2]2[CH:9]=[C:8]([C:10]3[C:11]([C:15]([F:16])([F:18])[F:17])=[N:12][NH:13][CH:14]=3)[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:22][CH2:21][CH2:20]1

참가 물질

6

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2734658(Bromomethyl)cyclobutaneHCID 178509603HCID 178509603, 화합물

생성물 1

HCID 1785096052-Cyclobutylmethylthio-4-(3-trifluoromethylpyrazolyl)benzonitrile수율 21.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

0.9 g (3.3 mmol) of 2-mercapto-4-(3-trifluoromethylpyrazolyl)benzonitrile, 0.5 g (3.3 mmol) of cyclobutylmethyl bromide and 0.55 g (4.0 mmol) of potassium carbonate were stirred in 5 ml of N,N-dimethylformamide at room temperature overnight. The resulting reaction mixture was poured into 50 ml of water and the organic matters were extracted with 20 ml of ethyl acetate twice. The ethyl acetate layers were combined, then washed with 30 ml of water twice and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. Purification of the residue by silica gel column chromatography afforded 0.24 g of 2-cyclobutylmethylthio-4-(3-trifluoromethylpyrazolyl)benzonitrile (yield 21.2%) as a pale yellow powder (m.p. 102-103° C.).

후처리

  1. customThe resulting reaction mixture
  2. extractionthe organic matters were extracted with 20 ml of ethyl acetate twice
  3. washwashed with 30 ml of water twice
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe ethyl acetate was distilled off under reduced pressure
  6. customPurification of the residue by silica gel column chromatography

출처 및 근거

ORD 기록
ord-109991864653475a9fb514957c60a928
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858639B2

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