Hydrochlorothiazide → 6-Chloro-2-(2-hydroxyethyl)-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide

HRID 747115

Reaktionsgleichung

Reaktionsgleichung von HRID 747115
[CH:1]1[C:6]([Cl:7])=[C:5]([S:8]([NH2:11])(=[O:10])=[O:9])[CH:4]=[C:3]2[S:12]([NH:15][CH2:16][NH:17][C:2]=12)(=[O:14])=[O:13].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:25][C:26](OCC)=[O:27]>CN(C=O)C>[Cl:7][C:6]1[C:5]([S:8]([NH2:11])(=[O:9])=[O:10])=[CH:4][C:3]2[S:12](=[O:14])(=[O:13])[N:15]([CH2:25][CH2:26][OH:27])[CH2:16][NH:17][C:2]=2[CH:1]=1

Komponenten

5

Edukt 3

HCID 3639HydrochlorothiazideHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonate

Produkt 1

HCID 597489496-Chloro-2-(2-hydroxyethyl)-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxideAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of hydrochlorothiazide (ONBIO, Inc., Ontario, Canada) (13.82 g, 46.4 mmol) in DMF (50 mL) was added cesium carbonate (7.51 g, 23.0 mmol) and ethyl bromoacetate (7.69 g, 46.1 mmol) and the mixture was stirred for 18 hours at room temperature. The solids were removed via suction filtration, and the solvent was evaporated under vacuum. The resulting residue was partitioned between ethyl acetate and water, and the organic layer was washed with water and brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was recrystallized from ethyl acetate/ether to give the title product (10.9 g, 61% yield) as white needles: mp 199-203° C.; 1H NMR (400 MHz, d6-DMSO) δ 8.07 (s, 1H), 8.01 (s, 1H), 7.53 (s, 2H), 7.08 (s, 1H), 4.97 (s, 2H), 4.14 (q, J=7.1 Hz, 2H), 3.82 (s, 2H), 1.19 (t, J=7.1 Hz, 3H); Mass spectrum (API-TIS) m/z 384 (MH+), 401 (MNH4+), 784 (2MNH430).

Aufarbeitung

  1. customThe solids were removed via suction filtration
  2. customthe solvent was evaporated under vacuum
  3. customThe resulting residue was partitioned between ethyl acetate and water
  4. washthe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customAfter evaporation of the solvent
  7. customthe residue was recrystallized from ethyl acetate/ether

Quellen und Nachweise

ORD-Eintrag
ord-aebca6518ad343d3a8a95338126f4285
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396829B2

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