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

HRID 1819919ノート

反応式

HRID 1819919 の反応式
[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]

参加物

5

反応物 3

HCID 1049PyridineHCID 62412tert-Butyl isocyanate2 回HCID 27947826,7,8,9-Tetrahydro-dibenzofuran-2-ylamine

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-06ff6d1d31a64478836532d68357153d
出典データセット
uspto-grants-2009_10
特許番号
US07601856B2

反応ノート

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