Sodium Iodide → 8-(3-Morpholinopropoxy)naphthalene-2-sulfonic acid

HRID 528804

反応式

HRID 528804 の反応式
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[C:9]([S:12]([OH:15])(=[O:14])=[O:13])[CH:8]=[CH:7]2.[OH-].[K+].Cl[CH2:19][CH2:20][CH2:21][N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.[Na+].[I-]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-].O>[O:25]1[CH2:26][CH2:27][N:22]([CH2:21][CH2:20][CH2:19][O:1][C:2]2[CH:3]=[CH:4][CH:5]=[C:6]3[C:11]=2[CH:10]=[C:9]([S:12]([OH:15])(=[O:13])=[O:14])[CH:8]=[CH:7]3)[CH2:23][CH2:24]1

参加物

8

反応物 4

HCID 5238Sodium IodideHCID 14797Potassium HydroxideHCID 958344-(3-Chloropropyl)morpholine2 回HCID 30224821-Hydroxynaphthalene-7-sulfonic acid2 回

生成物 1

HCID 867188648-(3-Morpholinopropoxy)naphthalene-2-sulfonic acid収率 31.9%

試薬・触媒・溶媒 3

HCID 67553Tetrabutylammonium Iodide触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a solution of 8-hydroxynaphthalene-2-sulfonic acid (Intermediate 26A, 300 mg, 1.34 mmol) and pulverized KOH (300 mg, 5.35 mmol) in DMF (2.0 mL) was added 4-(3-chloropropyl)morpholine (438 mg, 2.68 mmol) and NaI (401 mg, 2.68 mmol). The resulting reaction mixture was stirred at 60° C. for 12 h. TBAI (494 mg, 1.34 mmol) was then added followed by 4-(3-chloropropyl)morpholine (438 mg, 2.68 mmol). The reaction mixture was stirred at 60° C. for an additional 12 h, then diluted with water and filtered. The filtrate was purified directly using preparative HPLC to give the title compound (150 mg, 29%). 1H NMR (DMSO-d6) δ 8.49-8.34 (m, 1H), 7.80-7.70 (m, 1H), 7.70-7.60 (m, 1H), 7.36-7.19 (m, 2H), 6.89-6.77 (1 H, m), 3.95 (br s, 2H), 3.65 (br s, 4H), 3.48-3.32 (m, 2H), 3.26-3.06 (m, 2H), 2.57-2.44 (m, 2H), 2.37-2.13 (m, 2H); MS(ESI−) m/z 350.4 (M−H)−.

後処理

  1. customThe resulting reaction mixture
  2. stirringThe reaction mixture was stirred at 60° C. for an additional 12 h
  3. filtrationfiltered
  4. customThe filtrate was purified directly

出典と根拠

ORDレコード
ord-cbc1b18ba2834797ad18fc97e4776306
出典データセット
uspto-grants-2016_05
特許番号
US09346795B2

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