Bisphenol S → HCID 19758721, compound

HRID 1586640Notes

Reaction equation

HRID 1586640 reaction equation
C(N(CC)CC)C.Cl[CH:9]([C:35](=[O:48])[NH:36][C:37]1[CH:42]=[C:41]([C:43]([F:46])([F:45])[F:44])[CH:40]=[CH:39][C:38]=1[Cl:47])[C:10]([O:12][C:13]1[CH:34]=[CH:33][C:16]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:15][CH:14]=1)=[O:11].[S:49]([C:59]1[CH:64]=[CH:63][C:62]([OH:65])=[CH:61][CH:60]=1)([C:52]1[CH:57]=[CH:56][C:55]([OH:58])=[CH:54][CH:53]=1)(=[O:51])=[O:50]>CN(C=O)C>[Cl:47][C:38]1[CH:39]=[CH:40][C:41]([C:43]([F:46])([F:45])[F:44])=[CH:42][C:37]=1[NH:36][C:35]([CH:9]([O:58][C:55]1[CH:54]=[CH:53][C:52]([S:49]([C:59]2[CH:64]=[CH:63][C:62]([OH:65])=[CH:61][CH:60]=2)(=[O:51])=[O:50])=[CH:57][CH:56]=1)[C:10]([O:12][C:13]1[CH:34]=[CH:33][C:16]([O:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:15][CH:14]=1)=[O:11])=[O:48]

Participants

5

Reactant 3

HCID 6626Bisphenol SHCID 8471TriethylamineHCID 19758717HCID 19758717, compound

Product 1

HCID 19758721HCID 19758721, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Triethylamine (12.12 g, 120 mmol) was added to a solution of the chloro-coupler (24.5 g, 40.5 mmol) from (e) and 4,4'-sulfonyldiphenol (40.5 g, 162 mmol) in dry DMF (130 ml) which has been degassed with nitrogen. After stirring at 45°-50° C. under nitrogen for 1 h, the suspension was cooled and poured slowly into cold water (300 ml) and conc. hydrochloric acid (10 ml), with rapid stirring. The whole mixture was extracted with ethyl acetate (500 ml) and the organic solution washed with 3N sodium carbonate (2×400 ml), 3N hydrochloric acid (300 ml), dried over MgSO4 and evaporated under reduced pressure. The crude material was purified by silica gel column chromatography (gradient elution from 20% ethyl acetate in petrol (b.p. 60°-80° C.) to 60% ethyl acetate in petrol (b.p. 60°-80° C.) followed by recrystallization from methanol to give a white solid (13.5 g, 41%).

Workup

  1. customhas been degassed with nitrogen
  2. temperaturethe suspension was cooled
  3. additionpoured slowly into cold water (300 ml) and conc. hydrochloric acid (10 ml), with rapid stirring
  4. extractionThe whole mixture was extracted with ethyl acetate (500 ml)
  5. washthe organic solution washed with 3N sodium carbonate (2×400 ml), 3N hydrochloric acid (300 ml)
  6. dry with materialdried over MgSO4
  7. customevaporated under reduced pressure
  8. customThe crude material was purified by silica gel column chromatography (
  9. washgradient elution from 20% ethyl acetate in petrol (b.p. 60°-80° C.) to 60% ethyl acetate in petrol (b.p. 60°-80° C.)
  10. customfollowed by recrystallization from methanol

Sources & evidence

ORD record
ord-1e24e17b53ea44b79cab2ff6318552a4
Source dataset
uspto-grants-1993_06
Patent number
US05215878

Reaction notes

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