Lawesson's reagent → Ethyl 5-amino-1,3-thiazole-4-carboxylate

HRID 408833ノート

反応式

HRID 408833 の反応式
[CH:1]([NH:3][C@H:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]#[N:6])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:21])=CC=1>C1C=CC=CC=1>[NH2:6][C:5]1[S:21][CH:1]=[N:3][C:4]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

参加物

4

反応物 2

HCID 87949Lawesson's reagentHCID 86619658Ethyl N-formyl-3-nitriloalaninate

生成物 1

HCID 12620181Ethyl 5-amino-1,3-thiazole-4-carboxylate

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

Ethyl N-formyl-3-nitriloalaninate (11.22 g, 71.86 mmol) is dissolved in anhydrous benzene (220 mL). Following the addition of Lawesson's reagent (14.53 g, 35.93 mmol), the suspension is refluxed for 24 h. Most of the solvent is removed in vacuo, and the viscous red residue is absorbed on silica gel and loaded to a silica gel column (elution solvent: EtOAc:hexanes=50:50). The title compound is obtained as yellow solids. 1H NMR (400 MHz, CDCl3) 7.87 (1H, s), 7.26 (1 H, s), 6.01 (2H, broad s), 4.38 (2H, q), 1.41 (3H, t).

後処理

  1. temperaturethe suspension is refluxed for 24 h
  2. customMost of the solvent is removed in vacuo
  3. customthe viscous red residue is absorbed on silica gel
  4. washloaded to a silica gel column (elution solvent: EtOAc:hexanes=50:50)

出典と根拠

ORDレコード
ord-7eaf2e0f23d94fa7a31be1214a2b96db
出典データセット
uspto-grants-2014_06
特許番号
US08759361B2

反応ノート

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