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

HRID 2257771ノート

反応式

HRID 2257771 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: mp 187°-189° C.; MS (FD) m/e 282 (M+).

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-9ca3f4013afe4280bf3c3976c41ef8da
出典データセット
uspto-grants-1997_08
特許番号
US05658907

反応ノート

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