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Methanol → Methyl 2-(4-(4-chlorophenyl)-2-oxo-4-oxazolin-5-yl)propionate

HRID 47925
ノート
印刷プレビュー

反応式

HRID 47925 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][C:10](=[O:13])[O:11][CH:12]=2)=[CH:4][CH:3]=1.S(=O)(=O)(O)O.[C:19]([O:23][CH3:24])(=[O:22])[CH:20]=[CH2:21].CO>C(#N)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:9][C:10](=[O:13])[O:11][C:12]=2[CH:20]([CH3:21])[C:19]([O:23][CH3:24])=[O:22])=[CH:6][CH:7]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 7294Methyl AcrylateHCID 114241254-(4-Chlorophenyl)-2,3-dihydro-1,3-oxazol-2-one

生成物 1

HCID 11150230Methyl 2-(4-(4-chlorophenyl)-2-oxo-4-oxazolin-5-yl)propionate収率 79.4%

試薬・触媒・溶媒 2

HCID 962Water
溶媒
HCID 6342Acetonitrile溶媒

反応条件

温度
25 °C

実験手順

4-(4-chlorophenyl)-2-oxo-4-oxazoline (5.00 g) was suspended in acetonitrile (15 ml) in a reaction vessel, and the gas in the reaction vessel was substituted for nitrogen gas. The obtained suspension was cooled and conc. sulfuric acid (7.53 g) was added dropwise at 2-10° C. Then methyl acrylate (4.41 g) was added dropwise at 2-3° C. The obtained mixture was stirred at 20-30° C. for 1.5 h and methanol (15 ml) was added dropwise at 22-25° C. After cooling, water was added dropwise at 5-8° C. The precipitated crystals were collected by filtration, washed with water (25 ml), 1% aqueous sodium hydrogencarbonate (25 ml), water (25 ml) and diisopropyl ether (25 ml), and dried under reduced pressure at 40° C. for 7 h to give the title compound (5.72 g, yield 79.4%) as pale-red white crystals.

後処理

  1. temperatureThe obtained suspension was cooled
  2. temperatureAfter cooling
  3. filtrationThe precipitated crystals were collected by filtration
  4. washwashed with water (25 ml), 1% aqueous sodium hydrogencarbonate (25 ml), water (25 ml) and diisopropyl ether (25 ml)
  5. customdried under reduced pressure at 40° C. for 7 h

出典と根拠

ORDレコード
ord-87c3d32d56a648b0b9ca6c8647096520
出典データセット
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06699995B1

反応ノート

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