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

HRID 494441ノート

反応式

HRID 494441 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 14797Potassium Hydroxide溶媒

反応条件

温度
130 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4372c992d82d47bca9ed556d6c7642ec
出典データセット
uspto-grants-2009_05
特許番号
US07538105B2

反応ノート

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