Triethylamine → (5-Phenyl-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-3-yl)methanone

HRID 1904685

반응식

HRID 1904685 반응식
[C:1]1([CH:7]2[NH:11][N:10]=[CH:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl.[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[N:23][CH:22]=1>C(Cl)(Cl)Cl>[N:23]1[CH:24]=[CH:25][CH:26]=[C:21]([C:20]([N:11]2[CH:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:8][CH:9]=[N:10]2)=[O:27])[CH:22]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 1208415-Phenyl-4,5-dihydro-1H-pyrazole

생성물 1

HCID 3078467(5-Phenyl-4,5-dihydro-1H-pyrazol-1-yl)(pyridin-3-yl)methanone수율 86.3%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

A mixture of 5-phenyl-2-pyrazoline (2.9 g) and triethylamine (4 g) was added dropwise with ice cooling to a suspension of nicotinoyl chloride hydrochloride (4 g) in 20 ml chloroform, the resulting mixture was stirred for 15 minutes, washed with water and concentrated, and the concentrate was purified by silica gel chromatography (chloroform/methanol=100/1), giving 4.3 g (yield: 86%) of pure product. M.p. 100°-102° C.; NMR (CDCl3): 2.9-3.8 (2H, m), 5.61 (1H, dd, J=5, 12 Hz), 7.03 (1H, t, J=2 Hz), 7.31 (5H, s), 7.28 (1H, m), 8.15 (1H, dt, J=8, 2 Hz), 8.68 (1H, dd, J=2, 6 Hz), 9.13(1H, d, J=2 Hz).

후처리

  1. washwashed with water
  2. concentrationconcentrated
  3. customthe concentrate was purified by silica gel chromatography (chloroform/methanol=100/1)

출처 및 근거

ORD 기록
ord-6d56b42708264f458ab9c8c2ec6083c0
출처 데이터셋
uspto-grants-1989_06
특허 번호
US04839376

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