Isopropanol → 1-Isopropyl-4-nitro-1H-pyrazole

HRID 1854797노트

반응식

HRID 1854797 반응식
N(C(OC(C)(C)C)=O)=NC(O[C:6](C)([CH3:8])[CH3:7])=O.[N+:17]([C:20]1[CH:21]=[N:22][NH:23][CH:24]=1)([O-:19])=[O:18].CC(O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH:6]([N:22]1[CH:21]=[C:20]([N+:17]([O-:19])=[O:18])[CH:24]=[N:23]1)([CH3:8])[CH3:7]

참가 물질

6

반응물 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 163764-nitro-1H-pyrazoleHCID 97268Di-tert-butyl azodicarboxylate

생성물 1

HCID 134698241-Isopropyl-4-nitro-1H-pyrazole수율 149%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Di-tert-butyl azodicarboxylate (1.59 g, 6.91 mmol) was added to a solution of 4-nitro-1H-pyrazole (601 mg, 5.32 mmol), 2-propanol (319 mg, 5.32 mmol) and triphenylphosphine (1.67 g, 6.36 mmol) in tetrahydrofuran (25 mL) over 3 minutes and the mixture was stirred at room temperature for 16 h. After this time, the reaction was concentrated under reduced pressure and the resulting residue purified by chromatography (silica, gradient, 1:4 ethyl acetate/heptane to 7:3 ethyl acetate/heptane) to afford 1-isopropyl-4-nitro-1H-pyrazole (1) (1.23 g, >100%) as an impure off-white solid, which was used without further purification: 1H NMR (300 MHz, DMSO-d6) δ 8.91 (s, 1H), 8.24 (s, 1H), 4.58 (m, 1H), 1.42 (d, J=6.6 Hz, 6H).

후처리

  1. concentrationAfter this time, the reaction was concentrated under reduced pressure
  2. customthe resulting residue purified by chromatography (silica, gradient, 1:4 ethyl acetate/heptane to 7:3 ethyl acetate/heptane)

출처 및 근거

ORD 기록
ord-8474657a085841a2bb99f07f806ba1e0
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08962835B2

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