1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 13941691, compound

HRID 1885391Notes

Reaction equation

HRID 1885391 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([C:7](Cl)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1.[C:25]([O:31][C@@H:32]1[C@H:36]([O:37][S:38]([CH3:41])(=[O:40])=[O:39])[C@@H:35]([CH2:42][O:43][C:44](=[O:49])[C:45]([CH3:48])([CH3:47])[CH3:46])[O:34][C@H:33]1[N:50]1[CH:57]=[CH:56][C:54]([NH2:55])=[N:53][C:51]1=[O:52])(=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27].C(Cl)(Cl)Cl.C(OCC)(=O)C.C(N(CC)CC)C>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([C:7]([NH:55][C:54]2[CH:56]=[CH:57][N:50]([C@@H:33]3[O:34][C@H:35]([CH2:42][O:43][C:44](=[O:49])[C:45]([CH3:46])([CH3:47])[CH3:48])[C@@H:36]([O:37][S:38]([CH3:41])(=[O:40])=[O:39])[C@H:32]3[O:31][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])[C:51](=[O:52])[N:53]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 13941689HCID 13941689, compoundHCID 19764473HCID 19764473, compound

Product 1

HCID 13941691HCID 13941691, compoundYield 95.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent2×

Procedure

4,4'-Dimethoxytrityl chloride (685 mg, 2.02 mmol) was added to a solution of Compound C5 (825 mg, 1.69 mmol) in anhydrous pyridine (4 ml) and the mixture was stirred at room temperature for 3 hours. After cooling, aqueous 50% pyridine was added to decompose an excess of the reagent, and the mixture was extracted with ether containing a small amount of chloroform. The organic layer was washed with aqueous sodium bicarbonate and dried over magnesium sulfate. The organic solvents were evaporated, the remaining pyridine was removed as the toluene azeotrope and the residue was subjected to silica gel chromatography [eluant; chloroform-ethyl acetate-triethylamine (80:20:1)]to give 1.280 g of the desired compound, C6 (yield 96%).

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ether containing a small amount of chloroform
  3. washThe organic layer was washed with aqueous sodium bicarbonate
  4. dry with materialdried over magnesium sulfate
  5. customThe organic solvents were evaporated
  6. customthe remaining pyridine was removed as the toluene azeotrope

Sources & evidence

ORD record
ord-7e4450257b09449ab05733eb81a618ac
Source dataset
uspto-grants-1992_09
Patent number
US05144018

Reaction notes

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