Benzenesulfonyl chloride → Bis[4-(benzenesulfonyloxy)phenyl] Sulfide

HRID 1742557

反応式

HRID 1742557 の反応式
[S:1]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.[C:16]1([S:22](Cl)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:16]1([S:22]([O:8][C:5]2[CH:6]=[CH:7][C:2]([S:1][C:9]3[CH:14]=[CH:13][C:12]([O:15][S:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)(=[O:24])=[O:23])=[CH:11][CH:10]=3)=[CH:3][CH:4]=2)(=[O:24])=[O:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

参加物

5

反応物 2

HCID 7369Benzenesulfonyl chlorideHCID 175704,4'-Thiodiphenol

生成物 1

HCID 11841360Bis[4-(benzenesulfonyloxy)phenyl] Sulfide収率 98%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

実験手順

A 100 ml 3-necked oven-dried flask is equipped with a magnetic stirring bar and a CaCl2 -Drierite drying tube and is charged with 4,4'-thiodiphenol (5.3 grams, 24.3 mmol), benzenesulfonyl chloride (6.5 ml, 50.9 mmol), 4-dimethylaminopyridine (0.59 grams, 4.8 mmol), and anhydrous pyridine (40 ml). The mixture is stirred at ambient temperature for 18 hours, and at reflux for 4 hours, then is poured into ice-cold water (100 ml) with vigorous stirring, and the yellow oil that separates is extracted into CH2Cl2 (100 ml), and washed with water (100 ml). Drying (MgSO4), filtration and concentration affords a yellow oil. Purification by filtration through a column packed with flash-grade silica gel (5"×2" i.d.), eluting with CH2Cl2 (ca. 0.5 1), gives after solvent removal under vacuum 11.8 grams (98 percent yield) of the title compound as a faintly yellowish, thick glass material.

後処理

  1. customA 100 ml 3-necked oven-dried flask is equipped with a magnetic stirring bar and a CaCl2 -Drierite drying tube
  2. temperatureat reflux for 4 hours
  3. extractionthe yellow oil that separates is extracted into CH2Cl2 (100 ml)
  4. washwashed with water (100 ml)
  5. customDrying
  6. filtration(MgSO4), filtration and concentration
  7. customaffords a yellow oil
  8. customPurification
  9. filtrationby filtration through a column
  10. washeluting with CH2Cl2 (ca. 0.5 1)
  11. customgives

出典と根拠

ORDレコード
ord-5ea9559c3c394944b48d528ed0e455f4
出典データセット
uspto-grants-1994_08
特許番号
US05340489

関連ノート

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