Sodium Hydroxide → 5-amino-3-[(dibutylamino)methyl]-1-(phenylmethyl)-1H-pyrazole

HRID 373177

반응식

HRID 373177 반응식
[CH2:1]([N:5]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:6][C:7]#[C:8][C:9]#[N:10])[CH2:2][CH2:3][CH3:4].Cl.Cl.[CH2:17]([NH:24][NH2:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-].[Na+]>C(O)C>[NH2:10][C:9]1[N:24]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:25]=[C:7]([CH2:6][N:5]([CH2:11][CH2:12][CH2:13][CH3:14])[CH2:1][CH2:2][CH2:3][CH3:4])[CH:8]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 146540Benzylhydrazine dihydrochlorideHCID 198120394-Dibutylamino-2-butynenitrile

생성물 1

HCID 198120265-amino-3-[(dibutylamino)methyl]-1-(phenylmethyl)-1H-pyrazole수율 14.5%

시약·촉매·용매 1

HCID 702Ethanol용매2회

반응 조건

온도
25 °C

실험 절차

A solution of 4-dibutylamino-2-butynenitrile in ethanol (10 mL) was added to a stirring solution of benzylhydrazine dihydrochloride (3.0 g, 15.4 mmol) and 3.0 N NaOH (5.00 mL, 15.4 mmol) in ethanol (50 mL). The resulting solution as stirred (2 hours, 25° C.), then concentrated. The residue was taken up in ethyl acetate (250 mL), washed with brine (3×90 mL), then dried (MgSO4) and concentrated in vacuo. The resulting oil was chromatographed on silica (80:20 hexane:ethyl acetate) to yield 0.70 g (14.5%) of 5-amino-3-[(dibutylamino)methyl]-1-(phenylmethyl)-1H-pyrazole as an orange oil. 1H NMR (250 MHz, CDCl3 δ 7.22 (m, 6H), 4.56 (s, 2H), 4.00 (br s, 2H), 2.30 (m, 4H), 1.34 (m, 8H), 0.90 (t, 6H).

후처리

  1. concentrationconcentrated
  2. washwashed with brine (3×90 mL)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe resulting oil was chromatographed on silica (80:20 hexane:ethyl acetate)

출처 및 근거

ORD 기록
ord-7225b97783df47398193132e40b69031
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05162360

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