1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-(Azidomethyl)-1H-1,3-benzodiazole

HRID 397490

반응식

HRID 397490 반응식
O[CH2:2][C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][NH:9][C:5]=2[CH:4]=1.C1C=CC(P([N:26]=[N+:27]=[N-:28])(C2C=CC=CC=2)=O)=CC=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[N:26]([CH2:2][C:3]1[CH:11]=[CH:10][C:6]2[N:7]=[CH:8][NH:9][C:5]=2[CH:4]=1)=[N+:27]=[N-:28]

참가 물질

5

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 199401P,P-Diphenylphosphinic azideHCID 135055565-(Hydroxymethyl)-1H-benzimidazole

생성물 1

HCID 230001735-(Azidomethyl)-1H-1,3-benzodiazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a cooled (0° C.) suspension of 5-(hydroxymethyl)-benzimidazole (920 mg, 6.2 mmol) in THF (12 mL) was added sequentially DPPA (1.46 mL, 6.8 mmol) and DBU (1.11 mL, 7.4 mmol). The resulting solution was heated to reflux for 5 h, cooled to RT, and concentrated in vacuo. The residue was partitioned between sodium bicarbonate and ethyl acetate. The organic layer was washed with brine, dried (Na2SO4), and concentrated in vacuo. Silica gel chromatography (15% MeOH—CHCl3), afforded the title compound as a brown solid: Rf (8:1:1 EtOAc-MeOH—NH4H)=0.31; m.p. 110-114° C.; 1H NMR (400 MHz, DMSO-d6): δ8.25 (s, 1H), 7.27 (d, J=8.4, 1H), 7.62-7.60 (m, 2H), 7.20 (d, J=8.2 Hz, 1H), 8.24 (s, 1H); HRMS (FAB) C8H8N5 calcd. 174.1847 (M+1). Found 174.1222.

후처리

  1. temperatureTo a cooled
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 5 h
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between sodium bicarbonate and ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c08cae394226432fbd6efad8e8611001
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06610701B2

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