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

HRID 747115

反応式

HRID 747115 の反応式
[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

参加物

5

反応物 3

HCID 3639HydrochlorothiazideHCID 7748Ethyl bromoacetateHCID 10796Cesium carbonate

生成物 1

HCID 597489496-Chloro-2-(2-hydroxyethyl)-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide収率 69.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-aebca6518ad343d3a8a95338126f4285
出典データセット
uspto-grants-2008_07
特許番号
US07396829B2

関連ノート

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