Thioacetamide → HCID 20144971、化合物

HRID 1906004ノート

反応式

HRID 1906004 の反応式
[NH2:1][C:2]1[S:3][C:4]([C:12](=O)[CH2:13]Br)=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[C:16]([NH2:19])(=[S:18])[CH3:17]>COCCOC.C(O)C>[NH2:1][C:2]1[S:3][C:4]([C:12]2[N:19]=[C:16]([CH3:17])[S:18][CH:13]=2)=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1

参加物

5

反応物 2

HCID 2723949ThioacetamideHCID 20145096Ethyl 2-amino-5-(2-bromoacetyl)-4-thiazolecarboxylate

生成物 1

HCID 20144971HCID 20144971、化合物収率 64.8%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

A solution of ethyl 2-amino-5-(2-bromoacetyl)-4-thiazolecarboxylate (2.35 g) and thioacetamide (1.8 g) in a mixture of 1,2-dimethoxyethane (70 ml) and ethanol (70 ml) was refluxed for 7 hours and the reaction mixture was evaporated in vacuo. To the residue was added water, and the resulting mixture was adjusted to pH 8.0 with 20% aqueous potassium carbonate and extracted with a mixture of ethyl acetate and tetrahydrofuran. The extract was washed with brine, dried over magnesium sulfate, and evaported in vacuo. The residue was washed with diethyl ether and recrystallized from ethyl acetate to give ethyl 2-amino-5-(2-methyl-4-thiazolyl)-4-thiazolecarboxylate (1.4 g). mp 197°-199° C. (dec.)

後処理

  1. temperaturewas refluxed for 7 hours
  2. customthe reaction mixture was evaporated in vacuo
  3. additionTo the residue was added water
  4. extractionextracted with a mixture of ethyl acetate and tetrahydrofuran
  5. washThe extract was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. washThe residue was washed with diethyl ether
  8. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-9259cc6c52a14b599ceefc756af8c169
出典データセット
uspto-grants-1987_03
特許番号
US04649146

反応ノート

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