Sodium Iodide → HCID 19778670、化合物

HRID 374209

反応式

HRID 374209 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][CH:15]([CH2:18][NH2:19])[O:14][C:13]=2[CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:35]=[C:34]2[C:29]([CH:30]=[CH:31][C:32](=[O:36])[O:33]2)=[CH:28][CH:27]=1.C(N(C(C)C)CC)(C)C.[I-].[Na+]>CN(C=O)C>[C:2]1([CH2:1][O:8][C:9]2[CH:10]=[CH:11][C:12]3[O:17][CH2:16][CH:15]([CH2:18][NH:19][CH2:22][CH2:23][CH2:24][O:25][C:26]4[CH:27]=[CH:28][C:29]5[CH:30]=[CH:31][C:32](=[O:36])[O:33][C:34]=5[CH:35]=4)[O:14][C:13]=3[CH:20]=2)[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 81531DiisopropylethylamineHCID 19006662H-1-Benzopyran-2-one, 7-(3-chloropropoxy)-HCID 19778679HCID 19778679、化合物

生成物 1

HCID 19778670HCID 19778670、化合物収率 25.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2,3-Dihydro-7-benzyloxy-1,4-benzodioxin-2-methanamine (1.47 g, 5.42 mmole), 7-(3-chloropropoxy)coumarin (1.30 g, 5.45 mmole), diisopropylethylamine (4.0 ml, 23 mmole) and sodium iodide (4.17 g, 28 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, then 0.5% methanol/dichloromethane, and finally 1% methanol/dichloromethane as eluant. The fractions containing material with Rf=0.26 on silica gel tlc (2.5% methanol/chloroform) were combined and concentrated in vacuum and the residue crystallized from 50 ml of isopropanol with the addition of 4.0 ml of 4N isopropanolic HCl to give 0.66 g of title compound as an off-white solid, monohydrochloride, m.p. 179°-181° C.

後処理

  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. additionThe fractions containing material with Rf=0.26 on silica gel tlc (2.5% methanol/chloroform)
  9. concentrationconcentrated in vacuum
  10. customthe residue crystallized from 50 ml of isopropanol with the addition of 4.0 ml of 4N isopropanolic HCl

出典と根拠

ORDレコード
ord-1ae14f2b25dc4360b9c833fa61745dad
出典データセット
uspto-grants-1992_11
特許番号
US05166367

関連ノート

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