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Thiourea → Methyl 3-(2-amino-4-phenyl-5-thiazolyl)propionate

HRID 1295258
ノート
印刷プレビュー

反応式

HRID 1295258 の反応式
Br[CH:2]([C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6].[NH2:17][C:18]([NH2:20])=[S:19]>CO>[NH2:20][C:18]1[S:19][C:2]([CH2:3][CH2:4][C:5]([O:7][CH3:8])=[O:6])=[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:17]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 2723790ThioureaHCID 11066004Methyl 4-bromo-5-oxo-5-phenylpentanoate

生成物 1

HCID 22930733Methyl 3-(2-amino-4-phenyl-5-thiazolyl)propionate収率 90.6%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of methyl 4-bromo-5-oxo-5-phenylpentanoate (15.0 g), thiourea (3.81 g) and methanol (200 ml) was refluxed for 2 hrs. The reaction solvent was removed under reduced pressure, and the residue was dissolved in ethyl acetate. The obtained solution was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated to give methyl 3-(2-amino-4-phenyl-5-thiazolyl)propionate (11.9 g, yield 90%) as pale-yellow crystals. The crystals were recrystallized from ethyl acetate-hexane. melting point: 130–131° C.

後処理

  1. temperaturewas refluxed for 2 hrs
  2. customThe reaction solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe obtained solution was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-8bc7e2a7ff6742cf803f13f639de5d11
出典データセット
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07241785B2

反応ノート

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