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Benzo-1,3-dioxole-5-methylamine → 4-((1,3-Benzodioxol-5-ylmethyl)amino)-2,6-dichloro quinazoline

HRID 585093
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HRID 585093 반응식
[Cl:1][C:2]1[N:11]=[C:10](Cl)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Cl:13])[CH:8]=2)[N:3]=1.[CH2:14]([NH2:24])[C:15]1[CH:23]=[CH:22][C:21]2[O:20][CH2:19][O:18][C:17]=2[CH:16]=1>C(O)C>[O:20]1[C:21]2[CH:22]=[CH:23][C:15]([CH2:14][NH:24][C:10]3[C:9]4[C:4](=[CH:5][CH:6]=[C:7]([Cl:13])[CH:8]=4)[N:3]=[C:2]([Cl:1])[N:11]=3)=[CH:16][C:17]=2[O:18][CH2:19]1
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참가 물질

4

반응물 2

HCID 75799Benzo-1,3-dioxole-5-methylamineHCID 104215102,4,6-Trichloroquinazoline

생성물 1

HCID 223398654-((1,3-Benzodioxol-5-ylmethyl)amino)-2,6-dichloro quinazoline수율 96.2%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
55 °C

실험 절차

A solution of 2,4,6-trichloroquinazoline (0.186 g, 0.80 mmol) in ethanol (20 ml) was heated to 55° C. and piperonylamine (0.145 g, 0.96 mmol) was added. The resulting mixture was stirred at 55° C. over night. Volatiles were evaporated and the residue was partitioned between methylene chloride and saturated solution of ammonium hydroxide. The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo to yield 0.268 g (96% yield) of the title compound as a white solid. 1H NMR (300 MHz, DMSO) δ 4.59-4.63 (d, 2H), 5.98 (s, 2H), 6.86 (s, 2H), 6.96 (s, 1H), 7.62-7.66 (d, 1H), 7.79-7.84 (d, 1H), 8.46 (s, 1H), 9.24-9.28 (t,1H).

후처리

  1. customVolatiles were evaporated
  2. customthe residue was partitioned between methylene chloride and saturated solution of ammonium hydroxide
  3. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-f71b336ecbd14ceb93b756c708a78a53
출처 데이터셋
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06930113B2

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