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Formaldehyde → Ethyl 2-(5-phenylthiazolidin-4-on-3-yl)isobutyrate

HRID 355657
ノート
印刷プレビュー

反応式

HRID 355657 の反応式
Cl.[NH2:2][C:3]([CH3:10])([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].S[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]([OH:21])=O.C=O.C1(C)C=C[C:27]([S:30](O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.O.C(N(CC)CC)C>[C:13]1([CH:18]2[S:30][CH2:27][N:2]([C:3]([CH3:10])([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:19]2=[O:21])[CH:14]=[CH:15][CH:16]=[CH:17][CH:12]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 712FormaldehydeHCID 6101p-Toluenesulfonic acidHCID 51275252-Mercaptophenylacetic acidHCID 22343822Ethyl 2-amino-2-methylpropanoate hydrochloride

生成物 1

HCID 18940317Ethyl 2-(5-phenylthiazolidin-4-on-3-yl)isobutyrate

試薬・触媒・溶媒 3

HCID 962Water溶媒
HCID 1140
Toluene
溶媒
HCID 8471Triethylamine溶媒

実験手順

Triethylamine (3 g) was added to a suspension of ethyl 2-aminoisobutyrate hydrochloride (5 g) in toluene (60 mL) at room temperature. 2-Mercaptophenylacetic acid (6.44 g) was added to the mixture, which was then stirred at room temperature. After 10 minutes, a 35% formaldehyde aqueous solution (2.61 g) was added dropwise to the mixture. After the addition was completed, a catalytic amount of p-toluenesulfonic acid was added, and the mixture was allowed to react under heating at reflux for 4 hours, while water generated was excluded by azeotropic distillation from the reaction system. The reaction mixture was cooled to room temperature, to which ethyl acetate was added, and was then washed with a saturated sodium hydrogencarbonate aqueous solution and a saturated aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled under reduced pressure to give 5.49 g of the title compound as viscous oil.

後処理

  1. additionAfter the addition
  2. customto react
  3. temperatureunder heating
  4. distillationgenerated was excluded by azeotropic distillation from the reaction system
  5. temperatureThe reaction mixture was cooled to room temperature, to which ethyl acetate
  6. additionwas added
  7. washwas then washed with a saturated sodium hydrogencarbonate aqueous solution
  8. dry with materiala saturated aqueous sodium chloride and dried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled under reduced pressure

出典と根拠

ORDレコード
ord-1dba1b63eb9a4834be0247feb505f5fe
出典データセット
uspto-grants-1998_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05834401

反応ノート

読み込み中…

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