Water → 1-[4-(2-Azidoethyl)phenyl]-3,5-dimethyl-4-phenyl-1H-pyrazole

HRID 891079노트

반응식

HRID 891079 반응식
Cl[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([CH3:15])=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]([CH3:22])=[N:11]2)=[CH:6][CH:5]=1.[N-:23]=[N+:24]=[N-:25].[Na+].O>CN(C)C=O>[N:23]([CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([CH3:15])=[C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:12]([CH3:22])=[N:11]2)=[CH:6][CH:5]=1)=[N+:24]=[N-:25]

참가 물질

5

반응물 3

HCID 962WaterHCID 33557Sodium AzideHCID 222446901-[4-(2-Chloroethyl)phenyl]-3,5-dimethyl-4-phenyl-1H-pyrazole

생성물 1

HCID 222445571-[4-(2-Azidoethyl)phenyl]-3,5-dimethyl-4-phenyl-1H-pyrazole수율 81%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a stirred solution of 1-[4-(2-chloroethyl)phenyl]-3,5-dimethyl-4-phenyl-1H-pyrazole (step 1, 0.34 mmol) and KI (56 mg, 0.34 mmol) in N,N-dimethylformamide (2.7 mL) was added sodium azide (44 mg, 0.68 mmol), and then the resulting mixture was stirred for 6 h at 100° C. The reaction mixture was poured into water (100 mL), and extracted with ethyl acetate/toluene (4:1). The organic layer was washed with water (50 mL) and brine (50 mL), then dried (Na2SO4). After removal of the solvent, the crude product was purified by TLC with hexane/ethyl acetate (1:1) to afford 87 mg (81%) of the title compound as yellow oil: 1H-NMR (CDCl3) δ 7.46-7.29 (9H, m), 3.55 (2H, t, J=7.3 Hz), 2.96 (2H, t, J=7.1 Hz), 2.34 (3H, s), 2.30 (3H, s).

후처리

  1. extractionextracted with ethyl acetate/toluene (4:1)
  2. washThe organic layer was washed with water (50 mL) and brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. customAfter removal of the solvent
  5. customthe crude product was purified by TLC with hexane/ethyl acetate (1:1)

출처 및 근거

ORD 기록
ord-90fc3c277fba4d1b900563fedb3cf2bf
출처 데이터셋
uspto-grants-2006_02
특허 번호
US07001917B2

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