Methanol → 3,4-Dihydro-4-propyl-2H-1,2,4-benzothiadiazine-3-carboxylic acid 1,1-dioxide

HRID 617777

反応式

HRID 617777 の反応式
C[O:2][CH:3]([O:8]C)[C:4](OC)=O.CO.[CH2:12]([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22]([NH2:25])(=[O:24])=[O:23])[CH2:13][CH3:14].[OH-].[Na+]>O.O1CCOCC1>[CH2:12]([N:15]1[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[S:22](=[O:24])(=[O:23])[NH:25][CH:4]1[C:3]([OH:8])=[O:2])[CH2:13][CH3:14]

参加物

7

反応物 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 66647Acetic acid, 2,2-dimethoxy-, methyl esterHCID 218497762-(Propylamino)benzenesulfonamide

生成物 1

HCID 543318053,4-Dihydro-4-propyl-2H-1,2,4-benzothiadiazine-3-carboxylic acid 1,1-dioxide収率 44%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

実験手順

This compound was prepared according to the method of Close et. al., J. Org. Chem., 1961, 26, 3423-3433, incorporated by reference herein in its entirety. Thus, a solution of methyl dimethoxyacetate (3.6 g, 27.3 mmol) in water (50 l) was refluxed for 2.5 hours. A stillhead was attached and the methanol so generated was allowed to distill off (a total of 10 ml of liquid was collected, of which 5 ml was replenished with water). To the hot solution was added 2-(propylamino)benzenesulfonamide (4.5 g, 21.0 mmol) (prepared according to the procedure of Biressi et. al., Farmeco. Ed. Sci. (It.), 1969, 24, 199-220, incorporated by reference herein in its entirety) and 1,4-dioxane (5 ml, to give a homogeneous solution) and reflux was continued for 1.5 hours. The mixture was adjusted to pH 3 (2N NaOH), extracted with ethyl acetate and the organic phase was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated to give 4.8 g crude product which was recrystallized (ethyl acetate/hexanes) to give 2.5 g (44%) of the title compound as a white solid; NMR (DMSO-d6) δ 0.85 (t, J=7 Hz, 3H), 1.47-1.57 (m, 2H), 2.94-3.04 (m, 1H), 3.38 (br, 1H), 3.40-3.46 (m, 1H), 5.27 (d, J=6 Hz, 1H), 6.70 (t, J=7 Hz, 1H), 6.84 (d, J=7 Hz, 1H), 7.36 (t, J=7 Hz), 7.43 (d, J=7 Hz, 1H), 8.44 (d, J=7 Hz, 1H), 13.04 (br, 1H); MS: 269 m/z (M-H)- ; Anal. Calc'd for C11H14N2O4S: C, 48.88; H, 5.23; N, 10.37; S, 11.84; Found: C, 49.17; H, 5.21; N, 10.27; S, 11.54.

後処理

  1. customThis compound was prepared
  2. customof Close et. al., J
  3. distillationto distill off (a total of 10 ml of liquid
  4. customwas collected, of which 5 ml
  5. customprepared
  6. customto give a homogeneous solution) and
  7. temperaturereflux
  8. extractionextracted with ethyl acetate
  9. washthe organic phase was washed with brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated
  13. customto give 4.8 g crude product which
  14. customwas recrystallized (ethyl acetate/hexanes)

出典と根拠

ORDレコード
ord-144cc472774642bcb5c787fa87261500
出典データセット
uspto-grants-1999_09
特許番号
US05952328

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