Sodium hydride → 5-(3-Cyclohexyl-propoxy)-1-(4-nitro-phenyl)-1H-tetrazole

HRID 1004652

반응식

HRID 1004652 반응식
[CH:1]1([CH2:7][CH2:8][CH2:9][OH:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[C:14]1[N:18]([C:19]2[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=2)[N:17]=[N:16][N:15]=1>O1CCCC1>[CH:1]1([CH2:7][CH2:8][CH2:9][O:10][C:14]2[N:18]([C:19]3[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=3)[N:17]=[N:16][N:15]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 707633-Cyclohexyl-1-propanolHCID 15852121HCID 15852121, 화합물

생성물 1

HCID 224717005-(3-Cyclohexyl-propoxy)-1-(4-nitro-phenyl)-1H-tetrazole수율 68%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

Cyclohexylpropyl alcohol (237 mL, 1.56 mol) was added to a suspension of NaH (66.0 g, 1.65 mol) in tetrahydrofuran (1.40 L). A solution of 5-Chloro-1-(4-nitro-phenyl)-1H-tetrazole (320 g, 1.42 mol) in tetrahydrofuran (900 mL) was added dropwise over 1.5 hours. The reaction was allowed to cool to room temperature and stirred overnight. The mixture was concentrated in vacuo to a solid. The solid was dissolved in ethyl acetate, washed with saturated aqueous sodium chloride solution (2×), dried (Na2SO4), and filtered through silica gel (700 g). The red filtrate was concentrated in vacuo until product began to precipitate from solution. Hexane was added and the slurry filtered to provide a tan solid (320 g, 64%). Mp 82-88° C. (dec); 1H NMR (CDCl3, 300 MHz) δ 8.43 (d, 9.2 Hz, 2 H), 8.04 (d, 9.2 Hz, 2 H), 4.70 (t, 7.0 Hz, 2 H), 1.96 (m, 2 H), 1.75-1.64 (m, 5 H), 1.39-1.13 (m, 6 H), 0.97-0.87 (m, 2 H); MS (CI) m/z 332 (MH+); Anal. calcd for C16H21N5O3 : C, 57.99; H, 6.39; N, 21.13. Found: C, 57.80; H, 6.35; N, 21.02; Rf =0.43 (N).

후처리

  1. concentrationThe mixture was concentrated in vacuo to a solid
  2. dissolutionThe solid was dissolved in ethyl acetate
  3. washwashed with saturated aqueous sodium chloride solution (2×)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered through silica gel (700 g)
  6. concentrationThe red filtrate was concentrated in vacuo until product
  7. customto precipitate from solution
  8. additionHexane was added
  9. filtrationthe slurry filtered

출처 및 근거

ORD 기록
ord-4dd0786e892045d4b7824e43f875e8c5
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06051586

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