Ammonium Hydroxide → HCID 86753582、化合物

HRID 343085ノート

反応式

HRID 343085 の反応式
Cl[S:2]([OH:5])(=O)=[O:3].[CH3:6][S:7][C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[NH4+:26]>ClCCl>[CH3:6][S:7][C:8]1[O:12][N:11]=[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]=1[C:19]1[CH:24]=[CH:23][C:22]([S:2]([NH2:26])(=[O:5])=[O:3])=[CH:21][CH:20]=1

参加物

5

反応物 3

HCID 14923Ammonium HydroxideHCID 24638Chlorosulfonic acidHCID 53801427HCID 53801427、化合物

生成物 1

HCID 86753582HCID 86753582、化合物収率 30%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To stirred chlorosulfonic acid (3.0 mL, 45.06 mmol) at room temperature was carefully added solid 5-methylthio-3,4-diphenylisoxazole (Step 2) (0.915 g, 3.42 mmol). After 3 hours at room temperature, the reaction was poured over crushed ice. The resulting suspension was layered with dichloromethane and excess concentrated ammonium hydroxide and was stirred vigorously for 3 hours. The layers were separated and the aqueous layer extracted with ethyl acetate. The organic phases were combined, washed with aqueous KHSO4 solution (0.25N), aqueous NaHCO3 solution, and brine, dried over MgSO4, filtered and concentrated in vacuo yielding an oil. The oil was crystallized by dissolution in dichloromethane followed by the addition of isooctane until slight turbidity was seen. The resulting suspension was vacuum filtered yielding 4-[5-methylthio-3-phenylisoxazol-4-yl]benzenesulfonamide (0.355 g, 30%) as fine needles: mp 135°-137° C. 1H NMR (CDCl3 /300 MHz) 7.90 (d, 2H, J=8.5 Hz), 7.47-7.31 (m, 7 H), 4.81 (s, 2H), 2.69 (s, 3H). FABLRMS m/z 347 (M+H). FABHRMS m/z 347.0497(M+H, C16H15N2O3S2 requires 347.0524). Anal. Calc'd for C16H14N2O3S2.1.69 wt % H2O: C, 54.54; H, 4.19; N, 7.95. Found: C, 54.53; H, 4.04; N, 7.87.

後処理

  1. additionthe reaction was poured
  2. customover crushed ice
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with ethyl acetate
  5. washwashed with aqueous KHSO4 solution (0.25N), aqueous NaHCO3 solution, and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customyielding an oil
  10. customThe oil was crystallized by dissolution in dichloromethane
  11. additionfollowed by the addition of isooctane until slight turbidity
  12. filtrationfiltered

出典と根拠

ORDレコード
ord-6df3cd65edbf430a87394cdf0a1321bd
出典データセット
uspto-grants-1999_01
特許番号
US05859257

反応ノート

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