Bisphenol S → HCID 10974311、化合物

HRID 273672

反応式

HRID 273672 の反応式
[S:1]([C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[C:18]1([P:24](Cl)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:18]1([P:24]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([O:10][C:7]2[CH:8]=[CH:9][C:4]([S:1]([C:11]3[CH:16]=[CH:15][C:14]([O:17][P:24]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[O:25])=[CH:13][CH:12]=3)(=[O:3])=[O:2])=[CH:5][CH:6]=2)=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

5

反応物 2

HCID 6626Bisphenol SHCID 73910Diphenylphosphinic chloride

生成物 1

HCID 10974311HCID 10974311、化合物収率 94%

試薬・触媒・溶媒 2

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

実験手順

An oven-dried 100 mL 3-necked flask equipped with a magnetic stirring bar, a reflux condenser carrying a CaCl2 -Drierite drying tube, and a heating mantle, was charged with 4,4'-sulfonyldiphenol (3.9 g, 15.6 mmol), 4-dimethylaminopyridine (0.39 g, 3.2 mmol), and anhydrous pyridine (35 mL), and the stirred solution was treated slowly with diphenylphosphinyl chloride (6.5 mL, 34.1 mmol) via syringe. The resulting mixture was heated at reflux for 7 hours, then was allowed to stand at room temperature for 16 hours. The reaction was monitored periodically by HPLC. After completion of the reaction, the mixture was partitioned between water (100 mL) and CH2Cl2 -Et2O (1:3; 400 mL), and the organic phase was washed successively with 50 mL portions of 5 percent NaOH, water, 5 percent HCl, water and brine, then it was dried (MgSO4), filtered and concentrated leaving a white solid residue. Recrystallization from ethyl acetate-THF (9:1) afforded 9.5 g (94 percent yield) of the title compound as a white fluffy solid, m.p. 210-211° C. which had a PDSC (O2) onset/extrap (° C.) of 376/397.

後処理

  1. customAn oven-dried 100 mL 3-necked flask equipped with a magnetic stirring bar, a reflux condenser
  2. temperatureThe resulting mixture was heated
  3. temperatureat reflux for 7 hours
  4. customAfter completion of the reaction
  5. customthe mixture was partitioned between water (100 mL) and CH2Cl2 -Et2O (1:3; 400 mL)
  6. washthe organic phase was washed successively with 50 mL portions of 5 percent NaOH, water, 5 percent HCl, water and brine
  7. dry with materialit was dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customleaving a white solid residue
  11. customRecrystallization from ethyl acetate-THF (9:1)

出典と根拠

ORDレコード
ord-ca40cad95bd44aa0b580fad5583761b7
出典データセット
uspto-grants-1995_02
特許番号
US05387353

関連ノート

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