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Acrylonitrile → 3-Amino-1-(4-benzyloxy-2-fluorophenyl) pyrazoline

HRID 968670
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HRID 968670 반응식
C[O-].[Na+].[C:4](#[N:7])[CH:5]=[CH2:6].Cl.[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([NH:23][NH2:24])=[C:19]([F:25])[CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CO.CCOC(C)=O>[NH2:7][C:4]1[NH:24][N:23]([C:20]2[CH:21]=[CH:22][C:17]([O:16][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:18][C:19]=2[F:25])[CH2:6][CH:5]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 7855Acrylonitrile2회HCID 10942334Sodium Methoxide2회HCID 116375674-Benzyloxy-2-fluorophenylhydrazine hydrochloride

생성물 1

HCID 691586273-Amino-1-(4-benzyloxy-2-fluorophenyl) pyrazoline

시약·촉매·용매 2

HCID 887Methanol용매HCID 8857Ethyl Acetate
용매

실험 절차

NaOMe (25 wt. % solution in MeOH, 7.75 mL) and acrylonitrile (2.1 mL) were added to a solution of 4-benzyloxy-2-fluorophenylhydrazine hydrochloride (4.15 g) in MeOH (40 mL) at room temperature. The mixture was stirred at room temperature for 30 minutes and refluxed overnight. Additional NaOMe (25 wt. % solution in MeOH, 3.9 mL) and acrylonitrile (1.05 ml) were added to the reaction mixture and refluxed for 7.5 hours. The mixture was diluted with EtOAc and washed with sat. NaHCO3 and brine. The organic layer was dried over anhydrous MgSO4 and concentrated. The residue was crystallized from CHCl3/hexane to yield 3.86 g of the title compound. NaOMe and MeOH means sodium methoxide and methanol, respectively.

후처리

  1. temperaturerefluxed overnight
  2. temperaturerefluxed for 7.5 hours
  3. washwashed with sat. NaHCO3 and brine
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. concentrationconcentrated
  6. customThe residue was crystallized from CHCl3/hexane

출처 및 근거

ORD 기록
ord-843f1bab94fa4deeb927a63c1eb1c27e
출처 데이터셋
uspto-grants-2007_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07304072B2

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