Ethanol → Ethyl (7-hydroxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)acetate

HRID 30987ノート

反応式

HRID 30987 の反応式
OS(O)(=O)=O.[OH:6][C:7]1[CH:22]=[CH:21][C:10]2[NH:11][C:12]([CH2:17][C:18]([OH:20])=[O:19])=[N:13][S:14](=[O:16])(=[O:15])[C:9]=2[CH:8]=1.[CH3:23][CH2:24]O>>[CH2:23]([O:19][C:18](=[O:20])[CH2:17][C:12]1[NH:11][C:10]2[CH:21]=[CH:22][C:7]([OH:6])=[CH:8][C:9]=2[S:14](=[O:16])(=[O:15])[N:13]=1)[CH3:24]

参加物

4

反応物 3

HCID 702EthanolHCID 1118Sulfuric AcidHCID 11368865(7-Hydroxy-1,1-dioxo-1,4-dihydro-1lambda6-benzo[1,2,4]thiadiazin-3-yl)-acetic acid

生成物 1

HCID 46942308Ethyl (7-hydroxy-1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)acetate

反応条件

温度
80 °C

実験手順

EtOH (15 mL) and 150 μL of H2SO4 (conc.) were added into the compound 10c (5.03 mmol) and the mixture was heated to 80° C. for 45 minutes with stirring. The solvent was partially evaporated to half of the original volume under reduced pressure. EtOAc (30 mL) was added and the resulted mixture was washed with H2O (15 mL×3) via extraction. The aqueous layer was back extracted with EtOAc once (60 mL) and the combined organic layer was dried over anhydrous MgSO4, filtered, concentrated to give the desired product (4b) (1.11 g) as a gray solid. This crude material was directly used in next step without further purification. LC-MS: (ESI+) m/e=285.10 [M+1]+ (exact ms: 284.05).

後処理

  1. customThe solvent was partially evaporated to half of the original volume under reduced pressure
  2. additionEtOAc (30 mL) was added
  3. washthe resulted mixture was washed with H2O (15 mL×3) via extraction
  4. extractionThe aqueous layer was back extracted with EtOAc once (60 mL)
  5. dry with materialthe combined organic layer was dried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-c173e85b08924514b3c9533037c98213
出典データセット
uspto-grants-2008_09
特許番号
US07425552B2

反応ノート

読み込み中…