Chloroacetyl isocyanate → 2-[4-(2,4-dioxo-imidazolidin-1-yl)phenyl]-6-ethoxy-1-ethyl-1H-indole-3-carbonitrile

HRID 252548노트

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HRID 252548 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([CH2:22][CH3:23])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=3)=[CH:4][CH:3]=1.Cl[CH2:25][C:26]([N:28]=[C:29]=[O:30])=[O:27].C1CCN2C(=NCCC2)CC1>O1CCOCC1>[O:30]=[C:29]1[NH:28][C:26](=[O:27])[CH2:25][N:1]1[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([CH2:22][CH3:23])[C:10]3[C:15]([C:16]=2[C:17]#[N:18])=[CH:14][CH:13]=[C:12]([O:19][CH2:20][CH3:21])[CH:11]=3)=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 78209Chloroacetyl isocyanateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 594252742-(4-aminophenyl)-6-ethoxy-1-ethyl-1H-indole-3-carbonitrile

생성물 1

HCID 594249452-[4-(2,4-dioxo-imidazolidin-1-yl)phenyl]-6-ethoxy-1-ethyl-1H-indole-3-carbonitrile수율 79%

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

A solution of 2-(4-aminophenyl)-6-ethoxy-1-ethyl-1H-indole-3-carbonitrile (319 mg, 1.04 mmol) in 1,4-dioxane (3 mL) is treated with chloroacetyl isocyanate (0.10 mL, 1.17 mmol), and the resulting solution is warmed to 60° C. overnight. The solution is cooled, and DBU (0.20 mL, 1.31 mmol) is added. This mixture is stirred at ambient temperature overnight, and then is partitioned between water and ethyl acetate (50 mL each). The organic layer is washed with saturated brine, and then dried over anhydrous magnesium sulfate, filtered and evaporated. The residual material is triturated with ether, and the resulting solid is collected by filtration and dried under high vacuum to afford the title product (319 mg, 0.821 mmol, 79%).

후처리

  1. temperatureThe solution is cooled
  2. customis partitioned between water and ethyl acetate (50 mL each)
  3. washThe organic layer is washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residual material is triturated with ether
  8. filtrationthe resulting solid is collected by filtration
  9. customdried under high vacuum

출처 및 근거

ORD 기록
ord-b7abacf659a847fbafaf41713fa7b860
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868037B2

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