Dl-Phenylalanine → 3-Phenyl-5-(phenylmethyl)-2-thioxo-4-imidazolidinone

HRID 233692ノート

反応式

HRID 233692 の反応式
[NH2:1][CH:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:13]1([NH:19][C:20](=S)[S:21]C)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C>C(O)C>[CH2:3]([CH:2]1[NH:1][C:20](=[S:21])[N:19]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]1=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 994Dl-PhenylalanineHCID 8471TriethylamineHCID 3032344Methyl N-phenylcarbamodithioate

生成物 1

HCID 28719113-Phenyl-5-(phenylmethyl)-2-thioxo-4-imidazolidinone収率 88%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A solution of DL-phenylalanine (1.65 g, 10 mmol), methyl N-phenyldithiocarbamate (1.85 g, 10 mmol), and triethylamine (1.4 mL, 10 mmol) in ethanol (30 mL) was heated at reflux for 5 h, the mixture was cooled to room temperature and the solvent removed in vacuo. The residue was dissolved in ethyl acetate, washed with 1N aqueous HCl and water. The organic layer was concentrated and the residue recrystallized form ethanol to provide 2.48 g (88%) of the titled product:

後処理

  1. temperatureat reflux for 5 h
  2. customthe solvent removed in vacuo
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with 1N aqueous HCl and water
  5. concentrationThe organic layer was concentrated
  6. customthe residue recrystallized form ethanol

出典と根拠

ORDレコード
ord-a6bbfb22fbc64bb2957e594ca2a68965
出典データセット
uspto-grants-1997_01
特許番号
US05593993

反応ノート

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