2(3H)-Benzoxazolone → 6-Benzoxazolesulfonyl chloride, 2,3-dihydro-2-oxo-

HRID 641905

反応式

HRID 641905 の反応式
[S:1]([Cl:5])(=O)(=[O:3])[OH:2].[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]1=[O:15]>>[O:15]=[C:7]1[NH:8][C:9]2[CH:14]=[CH:13][C:12]([S:1]([Cl:5])(=[O:3])=[O:2])=[CH:11][C:10]=2[O:6]1

参加物

3

反応物 2

HCID 60432(3H)-BenzoxazoloneHCID 24638Chlorosulfonic acid

生成物 1

HCID 1196986-Benzoxazolesulfonyl chloride, 2,3-dihydro-2-oxo-収率 26%

反応条件

温度
0 °C

実験手順

Sulfurochloridic acid (70 g, 603.45 mmol) was cooled to 0° C. and benzo[d]oxazol-2(3H)-one (1.8 g, 13.33 mmol) was added in several batches, maintaining the temperature at about 0° C. The resulting solution was stirred at room temperature for 3 hours, then quenched by the addition 400 mL of iced water. The resulting solution was extracted with ethyl acetate (3×100 mL) and the organic layers were combined, dried (Na2SO4), filtered and concentrated. The residue was purified by column chromatography using a 1:10 ethyl acetate/petroleum ether solvent system to afford 0.8 g (26%) of 2-oxo-2,3-dihydrobenzo[d]oxazole-6-sulfonyl chloride as a white solid. 1H NMR (CDCl3) δ 8.26 (s, 1H), 8.00 (d, 1H), 7.98 (d, 1H), 7.32 (s, 1H).

後処理

  1. customquenched by the addition 400 mL of iced water
  2. extractionThe resulting solution was extracted with ethyl acetate (3×100 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-04afcd40b8324142a7fd20ccb96a99fd
出典データセット
uspto-grants-2010_04
特許番号
US07696229B2

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