1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 131727559, compound

HRID 2099890Notes

Reaction equation

HRID 2099890 reaction equation
[OH:1][CH:2]1[C:7]2([CH2:26][OH:27])[O:8][CH:9]([N:10]3[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:24])[C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[N:12][C:11]3=[O:25])[CH:3]1[O:4][N:5]([C:28](=[O:37])[CH2:29][O:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:6]2.[CH3:38][O:39][C:40]1[CH:61]=[CH:60][C:43]([C:44](Cl)(C2C=CC=CC=2)[C:45]2[CH:50]=[CH:49][C:48]([O:51][CH3:52])=[CH:47][CH:46]=2)=[CH:42][CH:41]=1>N1C=CC=CC=1>[CH3:52][O:51][C:48]1[CH:47]=[CH:46][C:45]([CH:44]([C:43]2[CH:42]=[CH:41][C:40]([O:39][CH3:38])=[CH:61][CH:60]=2)[O:27][CH:26]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:7]23[CH:2]([OH:1])[CH:3]([CH:9]([N:10]4[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:24])[C:18]5[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=5)=[N:12][C:11]4=[O:25])[O:8]2)[O:4][N:5]([C:28](=[O:37])[CH2:29][O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:6]3)=[CH:50][CH:49]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 131727560HCID 131727560, compound

Product 1

HCID 131727559HCID 131727559, compoundYield 165.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of Compound 67 (1.80 g, 3.54 mmol) in anhydrous pyridine (15 mL) was added 4-N,N-dimethylaminopyridine (65 mg, 0.53 mmol) and 4,4′-dimethoxytrityl chloride (2.04 g, 6.02 mmol). After stirring at room temperature for 6 hours the reaction mixture was quenched with methanol and concentrated in vacuo. The residue was dissolved in CH2Cl2 (300 mL), washed with saturated aqueous NaHCO3, dried over Na2SO4, filtered, and evaporated. Purification by silica gel chromatography (2% methanol in CH2Cl2) yielded 2.37 g (82%) of Compound 68 as a pale yellow foam.

Workup

  1. customwas quenched with methanol
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (300 mL)
  4. washwashed with saturated aqueous NaHCO3
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. customPurification by silica gel chromatography (2% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-9544909b63a14d8b918bf5cf5958e2b1
Source dataset
uspto-grants-2009_08
Patent number
US07569686B1

Reaction notes

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