Hexamethylenetetramine → HCID 86683416、化合物

HRID 579437ノート

反応式

HRID 579437 の反応式
C([O:3][C:4](=[O:20])[CH2:5][CH2:6][C:7]1[C:8](=[O:19])[O:9][C:10]2[C:15]([C:16]=1[CH3:17])=[CH:14][CH:13]=[C:12]([OH:18])[CH:11]=2)C.C1N2CN3CN(C2)CN1C3.FC(F)(F)[C:33](O)=[O:34]>>[CH:33]([C:11]1[C:12]([OH:18])=[CH:13][CH:14]=[C:15]2[C:10]=1[O:9][C:8](=[O:19])[C:7]([CH2:6][CH2:5][C:4]([OH:3])=[O:20])=[C:16]2[CH3:17])=[O:34]

参加物

4

反応物 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 5351036Ethyl 3-(7-hydroxy-4-methyl-2-oxo-2H-1-benzopyran-3-yl)propanoate

生成物 1

HCID 86683416HCID 86683416、化合物収率 13%

反応条件

温度
110 °C

実験手順

A mixture of 3-(7-hydroxy-4-methyl-2-oxo-2H-chromen-3-yl)-propionic acid ethyl ester (100 mg, 0.36 mmol) and hexamethylenetetramine (203 mg, 1.44 mmol) in trifluoroacetic acid (3.6 mL) was stirred in a closed vial under argon at 110° C. for 2 h. The reaction was poured onto crushed ice (15 mL), warmed to room temperature, and the solid precipitate was filtered off. This mixture of formylated ester and corresponding carboxylic acid was dissolved in dioxane-1N NaOH (1:1) and was stirred at room temperature. After 2 h, 15 mL of dichloromethane was added. The aqueous layer was separated and acidified by portionwise addition of 1N HCl. The precipitate was collected, washed with water, and dried to afford title compound (15 mg, 0.043 mmol, 13%) as a light brown powder.

後処理

  1. additionThe reaction was poured
  2. temperaturewarmed to room temperature
  3. filtrationthe solid precipitate was filtered off
  4. additionThis mixture of formylated ester and corresponding carboxylic acid
  5. dissolutionwas dissolved in dioxane-1N NaOH (1:1)
  6. stirringwas stirred at room temperature
  7. waitAfter 2 h
  8. addition15 mL of dichloromethane was added
  9. customThe aqueous layer was separated
  10. additionacidified by portionwise addition of 1N HCl
  11. customThe precipitate was collected
  12. washwashed with water
  13. customdried

出典と根拠

ORDレコード
ord-32e182ecb1624f4db2b7936491b8921d
出典データセット
uspto-grants-2015_05
特許番号
US09040714B2

反応ノート

読み込み中…