Pyridine → 1-Tert-butyl-3-(6,7,8,9-tetrahydro-dibenzofuran-2-yl)-urea

HRID 1819919노트

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HRID 1819919 반응식
[C:1]([N:5]=[C:6]=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:8]1[C:16]2[C:15]3[CH2:17][CH2:18][CH2:19][CH2:20][C:14]=3[O:13][C:12]=2[CH:11]=[CH:10][C:9]=1[NH2:21].N1C=CC=CC=1>O1CCCC1>[C:1]([NH:5][C:6]([NH:21][C:9]1[CH:10]=[CH:11][C:12]2[O:13][C:14]3[CH2:20][CH2:19][CH2:18][CH2:17][C:15]=3[C:16]=2[CH:8]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

5

반응물 3

HCID 1049PyridineHCID 62412tert-Butyl isocyanate2회HCID 27947826,7,8,9-Tetrahydro-dibenzofuran-2-ylamine

생성물 1

HCID 248978581-Tert-butyl-3-(6,7,8,9-tetrahydro-dibenzofuran-2-yl)-urea수율 49.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

tert-Butylisocyanate (0.55 g, 5.5 mmol) was added to a cooled (0° C.) solution of 6,7,8,9-tetrahydro-dibenzofuran-2-ylamine (0.94 g, 5.0 mmol) in tetrahydrofuran (20 mL). The reaction mixture was stirred for 10 minutes at 0° C. and then allowed to warm to ambient temperature for 5 hours. An additional portion of tert-butylisocyanate (0.65 mL) was added the reaction mixture was stirred overnight. The reaction was incomplete, so pyridine (10 mL) was added and the reaction mixture was heated to reflux for 4.5 hours and then concentrated under reduced pressure. The crude material was dissolved in ethyl acetate and washed with 1 N HCl, water, and brine, dried (Na2SO4) and concentrated. The crude material was recrystallized from acetonitrile to provide 1-tert-butyl-3-(6,7,8,9-tetrahydro-dibenzofuran-2-yl)-urea (0.71 g). Mp 310-312° C. (DEC); Anal. Calcd. for C17H22N2O2: C, 71.30; H, 7.74; N, 9.78; Found: C, 71.18; H, 7.84; N, 9.79.

후처리

  1. temperatureto warm to ambient temperature for 5 hours
  2. stirringwas stirred overnight
  3. temperaturethe reaction mixture was heated
  4. temperatureto reflux for 4.5 hours
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe crude material was dissolved in ethyl acetate
  7. washwashed with 1 N HCl, water, and brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated
  10. customThe crude material was recrystallized from acetonitrile

출처 및 근거

ORD 기록
ord-06ff6d1d31a64478836532d68357153d
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07601856B2

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