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Imidazole → 2-Chloro-5-(3-iodopropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide

HRID 1593833
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HRID 1593833 반응식
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24]O)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[I:26]I.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N1C=CN=C1>ClCCl>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][I:26])=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5]
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참가 물질

6

반응물 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 129886872-Chloro-5-(3-hydroxypropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

생성물 1

HCID 689262302-Chloro-5-(3-iodopropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)benzamide수율 88.4%

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

2-Chloro-5-(3-hydroxypropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (5.9 g, Example 6d), iodine (6.2 g, 24.4 mmol), triphenylphosphine (6.4 g, 24.4 mmol) and imidazole (1.66 g, 24.4 mmol) were stirred in dichloromethane (100 ml) at room temperature for 1 h. The reaction was quenched with sat. aq. Na2S2O3 and the layers were separated. The aqueous phase was extracted with ethyl acetate. The combined organic phases were dried (Na2SO4), concentrated and purified by column chromatography on silica (eluting with EtOAc:isohexane/1:3) to afford the subtitled compound as a pale yellow solid (6.8 g)

후처리

  1. customThe reaction was quenched with sat. aq. Na2S2O3
  2. customthe layers were separated
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialThe combined organic phases were dried (Na2SO4)
  5. concentrationconcentrated
  6. custompurified by column chromatography on silica (eluting with EtOAc:isohexane/1:3)

출처 및 근거

ORD 기록
ord-641de38b33044fa9ac403c91bb0fd5c0
출처 데이터셋
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07297818B2

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