Chlorosulfonic acid → 4-(Morpholin-4-yl)benzene-1-sulfonyl chloride

HRID 641901

反応式

HRID 641901 の反応式
[S:1]([Cl:5])(=O)(=[O:3])[OH:2].[C:6]1([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>>[O:15]1[CH2:16][CH2:17][N:12]([C:6]2[CH:11]=[CH:10][C:9]([S:1]([Cl:5])(=[O:3])=[O:2])=[CH:8][CH:7]=2)[CH2:13][CH2:14]1

参加物

3

反応物 2

HCID 24638Chlorosulfonic acidHCID 623394-Phenylmorpholine

生成物 1

HCID 149512114-(Morpholin-4-yl)benzene-1-sulfonyl chloride収率 14.7%

反応条件

温度
90 °C

実験手順

Sulfurochloridic acid (71.0 g, 612.07 mmol) was cooled to 0° C. and 4-phenylmorpholine (20.0 g, 122.53 mmol) was added in several batches, while keeping the temperature at 0° C. The resulting solution was then stirred at 90° C. for 20 hours. The reaction mixture was then added dropwise to 200 mL of ice/salt. The resulting solution was extracted with ethyl acetate (2×200 mL) and the organic layers were combined, dried (MgSO4) and filtered. The filtrate was concentrated, and the residue was purified by column chromatography using a 20:1 ethyl acetate/petroleum ether solvent system to give 4.7 g of 4-morpholinobenzene-1-sulfonyl chloride as a yellow solid. 1H NMR (CDCl3) δ 7.9 (d, 2H), 6.9 (d, 1H), 7.5 (d, 2H), 3.87 (t, 2H), 3.4 (t, 2H).

後処理

  1. customat 0° C
  2. extractionThe resulting solution was extracted with ethyl acetate (2×200 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified by column chromatography

出典と根拠

ORDレコード
ord-dcbef3f5dea44e39a7d60316e6e63e42
出典データセット
uspto-grants-2010_04
特許番号
US07696229B2

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