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

HRID 30987노트

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HRID 30987 반응식
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]

참가 물질

4

반응물 3

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

생성물 1

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

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-c173e85b08924514b3c9533037c98213
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425552B2

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