1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 131727558, compound

HRID 2099889Notes

Reaction equation

HRID 2099889 reaction equation
[OH:1][CH:2]1[C:7]2([CH2:18][OH:19])[O:8][CH:9]([N:10]3[CH:15]=[CH:14][C:13](=[O:16])[NH:12][C:11]3=[O:17])[CH:3]1[O:4][N:5]([CH3:20])[CH2:6]2.[CH3:21][O:22][C:23]1[CH:44]=[CH:43][C:26]([C:27](Cl)(C2C=CC=CC=2)[C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[CH:25][CH:24]=1>N1C=CC=CC=1>[CH3:35][O:34][C:31]1[CH:30]=[CH:29][C:28]([CH:27]([C:26]2[CH:25]=[CH:24][C:23]([O:22][CH3:21])=[CH:44][CH:43]=2)[O:19][CH:18]([C:23]2[CH:44]=[CH:43][CH:26]=[CH:25][CH:24]=2)[C:7]23[CH:2]([OH:1])[CH:3]([CH:9]([N:10]4[CH:15]=[CH:14][C:13](=[O:16])[NH:12][C:11]4=[O:17])[O:8]2)[O:4][N:5]([CH3:20])[CH2:6]3)=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 68902706HCID 68902706, compound

Product 1

HCID 131727558HCID 131727558, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of compound 55 (1 mmol) in anhydrous pyridine (4 mL) was added 4,4′-dimethoxytrityl chloride (1.5 mmol). After stirring at room temperature for 6 hours the mixture was quenched with MeOH and then concentrated in vacuo. The residue was dissolved in CH2Cl2 (100 mL), washed with saturated aqueous NaHCO3 (2×20 mL), brine (20 mL) and the organic layer dried over Na2SO4, filtered, and evaporated. The residue was purified by silica gel chromatography. Appropriate fractions were collected, concentrated to give compound 56 in 80% yield.

Workup

  1. customwas quenched with MeOH
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (100 mL)
  4. washwashed with saturated aqueous NaHCO3 (2×20 mL), brine (20 mL)
  5. dry with materialthe organic layer dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by silica gel chromatography
  9. customAppropriate fractions were collected
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-d52007e52dcf4cdd83097c44dcf39fc0
Source dataset
uspto-grants-2009_08
Patent number
US07569686B1

Reaction notes

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