Bisphenol S → HCID 10974311, 화합물

HRID 273672

반응식

HRID 273672 반응식
[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

참가 물질

5

반응물 2

HCID 6626Bisphenol SHCID 73910Diphenylphosphinic chloride

생성물 1

HCID 10974311HCID 10974311, 화합물수율 94%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ca40cad95bd44aa0b580fad5583761b7
출처 데이터셋
uspto-grants-1995_02
특허 번호
US05387353

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