Sodium Iodide → HCID 9885549, 화합물

HRID 374207

반응식

HRID 374207 반응식
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][NH2:12].Cl[CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:27]=[C:26]2[C:21]([CH:22]=[CH:23][C:24](=[O:28])[O:25]2)=[CH:20][CH:19]=1.C(N(C(C)C)CC)(C)C.[I-].[Na+]>CN1CCCC1=O>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3][CH:2]1[CH2:11][NH:12][CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:19]=[CH:20][C:21]2[CH:22]=[CH:23][C:24](=[O:28])[O:25][C:26]=2[CH:27]=1

참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 150532-Aminomethyl-1,4-benzodioxaneHCID 81531DiisopropylethylamineHCID 19006662H-1-Benzopyran-2-one, 7-(3-chloropropoxy)-

생성물 1

HCID 9885549HCID 9885549, 화합물수율 29.9%

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

반응 조건

온도
80 °C

실험 절차

2,3-Dihydro-1,4-benzodioxin-2-methanamine (1.7 g, 10 mmole), 7-(3-chloropropoxy)coumarin (2.4 g, 10 mmole), diisopropylethylamine (1.3 g, 10 mmole) and sodium iodide (5.0 g, 33 mmole) were combined in 100 ml of N-methylpyrrolidinone and heated at 80° C. for 24 hours under a nitrogen atmosphere. The solvent was then removed and replaced with 300 ml of dichloromethane. The mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, with saturated aqueous sodium chloride, dried over sodium sulfate, filtered, and concentrated in vacuum. The residue was column chromatographed on 100 g of silica gel using chloroform as eluant. The product-containing fractions (Rf=0.15 on silica gel tlc with 1% methanol/chloroform) were combined and concentrated in vacuum and the residue crystallized from isopropanol with the addition of 4N isopropanolic HCl to give 1.1 g of title compound as a tan solid, monohydrochloride, m.p. 213°-215° C.

후처리

  1. customThe solvent was then removed
  2. washThe mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, with saturated aqueous sodium chloride
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customchromatographed on 100 g of silica gel
  7. concentrationconcentrated in vacuum
  8. customthe residue crystallized from isopropanol with the addition of 4N isopropanolic HCl

출처 및 근거

ORD 기록
ord-24131e64abc0474cb11da098bc0aaf39
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05166367

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