Lawesson's reagent → Ethyl 5-amino-2-methylthiazole-4-carboxylate

HRID 1365834

反応式

HRID 1365834 の反応式
[CH2:1]([O:3][C:4](=[O:12])[CH:5]([NH:8][C:9](=O)[CH3:10])[C:6]#[N:7])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:22])=CC=1>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:5]1[N:8]=[C:9]([CH3:10])[S:22][C:6]=1[NH2:7])=[O:12])[CH3:2]

参加物

4

反応物 2

HCID 87949Lawesson's reagentHCID 95422Ethyl acetamidocyanoacetate

生成物 1

HCID 13329095Ethyl 5-amino-2-methylthiazole-4-carboxylate収率 115.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To a solution of acetylamino-cyano-acetic acid ethyl ester (27.2 g, 0.160 mol) in anhydrous toluene (300 mL) was added Lawesson's reagent (32.0 g, 0.079 mol) and the resulting mixture heated at reflux for 18 h. The resulting yellow suspension was partitioned between an aqueous solution of HCl (1 M) and tert-butyl methyl ether. The layers were separated and the organic layer extracted with an aqueous solution of HCl (1 M). The combined aqueous layers was basified to pH 10 with an aqueous solution of NaOH (2 M), then extracted with EtOAc. The organic layer was isolated, dried (Na2SO4) and concentrated in vacuo to give the title compound as a pale yellow solid (17.0 g, 57%).

後処理

  1. temperaturethe resulting mixture heated
  2. temperatureat reflux for 18 h
  3. customThe resulting yellow suspension was partitioned between an aqueous solution of HCl (1 M) and tert-butyl methyl ether
  4. customThe layers were separated
  5. extractionthe organic layer extracted with an aqueous solution of HCl (1 M)
  6. extractionextracted with EtOAc
  7. customThe organic layer was isolated
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-304406e4e3014777a678972d9ac96a6c
出典データセット
uspto-grants-2011_02
特許番号
US07893060B2

関連ノート

読み込み中…