Sodium Iodide → HCID 19778675、化合物

HRID 374210

反応式

HRID 374210 の反応式
[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]2[O:13][CH:14]([CH2:17][NH2:18])[CH2:15][O:16][C:11]=2[CH:10]=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:20]=[CH:19][C:12]3[O:13][CH:14]([CH2:17][NH:18][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)[CH2:15][O:16][C:11]=3[CH:10]=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 197786802,3-Dihydro-6-benzyloxy-1,4-benzodioxin-2-methanamine

生成物 1

HCID 19778675HCID 19778675、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
108 °C

実験手順

2,3-Dihydro-6-benzyloxy-1,4-benzodioxin-2-methanamine (2.4 g, 8.85 mmole), 7-(3-chloropropoxy)coumarin (2.15 g, 9.0 mmole), diisopropylethylamine (7.0 ml, 40.2 mmole) and sodium iodide (1.35 g, 9.0 mmole) were combined in 200 ml of DMF and heated at 108° 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 water dried over magnesium sulfate, filtered, and concentrated in vacuum. The residue was column chromatographed on silica gel using 1% methanol/dichloromethane as eluant. The product-containing fractions (Rf=0.27 on silica gel tlc with 2.5% methanol/dichloromethane) were combined and concentrated in vacuum and the residue redissolved in dichloromethane and boiled on a hot plate, the solvent gradually being replaced with isopropanol. Upon addition of 6 ml of 4N HCl/isopropanol and cooling, 1.22 g of the title compound, m.p. 184°-187° C., precipitated as a beige solid, monohydrochloride.

後処理

  1. customThe solvent was then removed
  2. washThe mixture was washed with an equal volume of water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuum
  6. customchromatographed on silica gel using 1% methanol/dichloromethane as eluant
  7. concentrationconcentrated in vacuum
  8. dissolutionthe residue redissolved in dichloromethane
  9. additionUpon addition of 6 ml of 4N HCl/isopropanol
  10. temperaturecooling
  11. custom1.22 g of the title compound, m.p. 184°-187° C., precipitated as a beige solid, monohydrochloride

出典と根拠

ORDレコード
ord-455b62b6cefc4a728535c01e75dff804
出典データセット
uspto-grants-1992_11
特許番号
US05166367

関連ノート

読み込み中…