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Acetic Acid → 2,3-dihydro-3-oxo-5H-thiazolo[2,3-b]quinazoline-2-acetic acid methyl ester

HRID 280376
ノート
印刷プレビュー

反応式

HRID 280376 の反応式
[BH4-].[Na+].[Te].C(O)(=O)C.[CH3:8][O:9][C:10](=[O:26])[CH:11]=[C:12]1[S:24][C:15]2=[N:16][C:17]3[C:22]([CH2:23][N:14]2[C:13]1=[O:25])=[CH:21][CH:20]=[CH:19][CH:18]=3>C(O)C>[CH3:8][O:9][C:10](=[O:26])[CH2:11][CH:12]1[S:24][C:15]2=[N:16][C:17]3[C:22]([CH2:23][N:14]2[C:13]1=[O:25])=[CH:21][CH:20]=[CH:19][CH:18]=3
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 6327182TelluriumHCID 54051732(3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetic acid methyl ester

生成物 1

HCID 136490782,3-dihydro-3-oxo-5H-thiazolo[2,3-b]quinazoline-2-acetic acid methyl ester収率 32.3%

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒
3 回

反応条件

温度
-20 °C

実験手順

A suspension of sodium borohydride (3.03 g, 0.08 mol) and 4.38 g (0.034 mol) tellurium powder in 135 ml anhydrous ethanol was heated under nitrogen atmosphere for 15 min. After cooling to -20° C., 8.08 ml glacial acetic acid in 33.65 ml anhydrous ethanol was added dropwise, and the mixture was stirred at that temperature for 5 min, followed by the addition of 3.50 g (0.013 mol) of (3-oxo-5H-thiazolo[2,3-b]quinazolin-2(3H)-ylidene)acetic acid methyl ester in 13.5 ml anhydrous ethanol. The reaction mixture was allowed to warm up to ambient temperature and stirred overnight. Then, the mixture was filtered through celite, and evaporated under reduced pressure. The residue was taken up in water and extracted with chloroform. The organic extract was dried over anhydrous magnesium sulfate and evaporated under reduced pressure, yielding 1.16 g of 2,3-dihydro-3-oxo-5H-thiazolo[2,3-b]quinazoline-2-acetic acid methyl ester. Mp 143°-144° C. after recrystallization from ethyl acetate.

後処理

  1. temperaturewas heated under nitrogen atmosphere for 15 min
  2. temperatureto warm up to ambient temperature
  3. stirringstirred overnight
  4. filtrationThen, the mixture was filtered through celite
  5. customevaporated under reduced pressure
  6. extractionextracted with chloroform
  7. extractionThe organic extract
  8. dry with materialwas dried over anhydrous magnesium sulfate
  9. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-f5731bc72c454b01b975e3e4261ed7dd
出典データセット
uspto-grants-1986_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04588812

反応ノート

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