Citric Acid → 3-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1,1-dipropyl-2(1H)-naphthalenone

HRID 494441노트

반응식

HRID 494441 반응식
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[NH:11][C:12]([C:14]1[C:23](=[O:24])[C:22]([CH2:28][CH2:29][CH3:30])([CH2:25][CH2:26][CH3:27])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]=1[OH:31])=O)(=[O:4])=[O:3].C(O)(=O)CC(CC(O)=O)(C(O)=O)O.C(OCC)(=O)C>[OH-].[K+]>[O:4]=[S:2]1(=[O:3])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[NH:11][C:12]([C:14]2[C:23](=[O:24])[C:22]([CH2:28][CH2:29][CH3:30])([CH2:25][CH2:26][CH3:27])[C:21]3[C:16]([C:15]=2[OH:31])=[CH:17][CH:18]=[CH:19][CH:20]=3)=[N:1]1

참가 물질

5

반응물 3

HCID 311Citric AcidHCID 8857Ethyl AcetateHCID 54723969N-[2-(aminosulfonyl)phenyl]-1-hydroxy-3-oxo-4,4-dipropyl-3,4-dihydro-2-naphthalenecarboxamide

생성물 1

HCID 1355144473-(1,1-dioxido-4H-1,2,4-benzothiadiazin-3-yl)-4-hydroxy-1,1-dipropyl-2(1H)-naphthalenone수율 57.5%

시약·촉매·용매 1

HCID 14797Potassium Hydroxide용매

반응 조건

온도
130 °C

실험 절차

A suspension of the product of Example 1G (150 mg, 0.34 mmol) in 10% potassium hydroxide solution (9 mL) was stirred at 130° C. for 30 hours, cooled to 25° C., acidified to pH 3 by addition of 1 M citric acid, stirred with ethyl acetate, and filtered through Celite®. The organic layer from the filtrate was washed with saturated sodium chloride solution, dried (Na2SO4), filtered and concentrated in vacuo. The residue was recrystallized from ether-hexane solution to afford the title compound (83 mg, 57%). 1H NMR (300 MHz, CDCl3): δ16.70 (s, 1 H), 14.22 (s, 1 H), 8.26 (d, J=8.09 Hz, 1 H), 7.99 (d, J=8.09 Hz, 1 H), 7.67 (m, 1H), 7.47 (m, 3 H), 7.29 (m, 2 H), 2.25 (m, 2 H), 1.86 (m, 2 H), 0.89 (m, 2 H), 0.70 (m, 8 H).

후처리

  1. temperaturecooled to 25° C.
  2. filtrationfiltered through Celite®
  3. washThe organic layer from the filtrate was washed with saturated sodium chloride solution
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was recrystallized from ether-hexane solution

출처 및 근거

ORD 기록
ord-4372c992d82d47bca9ed556d6c7642ec
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07538105B2

반응 노트

불러오는 중…