Butylamine → N,N-dibutyl-4-chloro-5-methyl-1H-pyrazole-3-carboxamide

HRID 528788

반응식

HRID 528788 반응식
[CH2:1]([NH2:5])[CH2:2][CH2:3][CH3:4].[Li][CH2:7][CH2:8][CH2:9][CH3:10].[Cl:11][C:12]1[C:13]([C:18]([O:20]CC)=O)=[N:14][NH:15][C:16]=1[CH3:17]>C1COCC1>[CH2:1]([N:5]([CH2:7][CH2:8][CH2:9][CH3:10])[C:18]([C:13]1[C:12]([Cl:11])=[C:16]([CH3:17])[NH:15][N:14]=1)=[O:20])[CH2:2][CH2:3][CH3:4]

참가 물질

5

반응물 3

HCID 8007ButylamineHCID 604759ethyl 4-chloro-5-methyl-1H-pyrazole-3-carboxylateHCID 178418339Butyllithium

생성물 1

HCID 71062189N,N-dibutyl-4-chloro-5-methyl-1H-pyrazole-3-carboxamide수율 82%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

To a solution of n-butylamine (900 μL, 5.30 mmol) in THF (4.0 mL) was added n-BuLi (5.0 mL, 7.95 mmol, 2.5M solution in hexanes) at −78° C. After stirring at −78° C. for 30 min, a solution of ethyl 4-chloro-5-methyl-1H-pyrazole-3-carboxylate (500 mg, 2.65 mmol) in 2.0 mL of THF was added dropwise via syringe. The reaction mixture was allowed to warm to room temperature overnight and quenched with sat. aq. NH4Cl solution. The aqueous layer was extracted with CH2Cl2 (3×), and the combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to give a crude oil. Purification using flash column chromatography (gradient from 0% to 7% MeOH/CH2Cl2) provided the title compound (589 mg, 82%) as a colorless oil. 1H NMR (CD3OD) δ 3.51 (t, J=7.4 Hz, 2H), 3.38-3.32 (m, 2H), 1.68-1.62 (m, 2H), 1.56-1.50 (m, 2H), 1.45-1.38 (m, 2H), 1.22-1.15 (m, 2H) 0.98 (t, J=7.4 Hz, 3H), 0.81 (t, J=7.4 Hz, 3H); MS(ESI+) m/z 272.1 (M+H)+.

후처리

  1. temperatureto warm to room temperature overnight
  2. customquenched with sat. aq. NH4Cl solution
  3. extractionThe aqueous layer was extracted with CH2Cl2 (3×)
  4. dry with materialthe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a crude oil
  8. customPurification

출처 및 근거

ORD 기록
ord-24a83f24190a4d58aa6016eab1c3e639
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346795B2

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