Sodium Iodide → HCID 19778665, 화합물

HRID 374212

반응식

HRID 374212 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]([CH2:11][NH2:12])[O:7][C:6]=2[CH:13]=1.Cl[CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:28]=[C:27]2[C:22]([CH:23]=[CH:24][C:25](=[O:29])[O:26]2)=[CH:21][CH:20]=1.C(N(C(C)C)CC)(C)C.[I-].[Na+].Cl.CC(O)C>CN(C=O)C.CO.C(O)(C)C>[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH:8]([CH2:11][NH:12][CH2:15][CH2:16][CH2:17][O:18][C:19]3[CH:20]=[CH:21][C:22]4[CH:23]=[CH:24][C:25](=[O:29])[O:26][C:27]=4[CH:28]=3)[O:7][C:6]=2[CH:13]=1

참가 물질

9

반응물 5

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 19006662H-1-Benzopyran-2-one, 7-(3-chloropropoxy)-HCID 18923891HCID 18923891, 화합물HCID 21912024Isopropanol hydrochloride

생성물 1

HCID 19778665HCID 19778665, 화합물수율 16%

시약·촉매·용매 3

HCID 887Methanol용매2회HCID 3776Isopropanol용매HCID 6228Dimethylformamide용매

실험 절차

2,3-Dihydro-7-hydroxy-1,4-benzodioxin-2-methanamine (3.00 g, 16.6 mmole), 7-(3-chloropropoxy)coumarin (2.95 g, 12.4 mmole), diisopropylethylamine (8.0 ml, 46.0 mmole) and sodium iodide (2.58 g, 17.2 mmole) were combined in 150 ml of DMF and heated at 80°-100° C. for 2 days under a nitrogen atmosphere. The solvent was then removed and replaced with dichloromethane. The mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, with saturated aqueous sodium chloride, dried over magnesium sulfate, filtered, and concentrated in vacuum. The residue was column chromatographed on silica gel using first dichloromethane and then 0.25% methanol/dichloromethane as eluant. The product-containing fractions were combined and concentrated in vacuum and the pure free base (1.0 g, an additional 2.0 g were obtained of lower purity) redissolved in methanol and boiled on a hot plate, the methanol gradually being replaced with isopropanol. 4N HCl/IPA was added and the title compound was collected by filtration and dried in vacuum at 80° C. The procedure yielded 0.76 g of beige solid, monohydrochloride, m.p. 252° C. (d).

후처리

  1. temperatureheated at 80°-100° C. for 2 days under a nitrogen atmosphere
  2. customThe solvent was then removed
  3. washThe mixture was washed with an equal volume of saturated aqueous sodium bicarbonate, with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. customchromatographed on silica gel using first dichloromethane
  8. concentrationconcentrated in vacuum
  9. customthe pure free base (1.0 g, an additional 2.0 g were obtained of lower purity)
  10. filtrationthe title compound was collected by filtration
  11. customdried in vacuum at 80° C

출처 및 근거

ORD 기록
ord-37ea97c2bcb44e0db0b441e64c640a41
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05166367

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