1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 69621284, compound

HRID 254918Notes

Reaction equation

HRID 254918 reaction equation
[C@@H:1]1([N:10]2[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]2=[O:12])[S:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]1[OH:3].[CH3:18][O:19][C:20]1[CH:41]=[CH:40][C:23]([C:24](Cl)([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=2)=[CH:22][CH:21]=1>N1C=CC=CC=1>[CH3:32][O:31][C:28]1[CH:27]=[CH:26][C:25]([C:24]([CH:8]([OH:9])[C@H:6]2[S:7][C@@H:1]([N:10]3[CH:17]=[CH:16][C:14](=[O:15])[NH:13][C:11]3=[O:12])[C@H:2]([OH:3])[C@@H:4]2[OH:5])([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:23]2[CH:40]=[CH:41][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 112191494′-Thiouridine

Product 1

HCID 69621284HCID 69621284, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 13 (2 g, 7.754 mmol) was dissolved in dry pyridine (20 mL), 4,4′-dimethoxytrityl chloride (2.9 g, 8.53 mmol) was added and the mixture stirred at room temperature overnight. The reaction was quenched with methanol and taken up in ethyl acetate (200 mL). The ethyl acetate solution was washed twice with saturated sodium bicarbonate solution, once with water, once with brine, and dried over anhydrous sodium sulfate. The solvents were removed under reduced pressure and the residue purified by flash chromatography (7% methanol in dichloromethane). The desired fractions were pooled and concentrated to give Compound 14 (3.0 g) in 80% yield. The structure of Compound 14 was confirmed by 1H NMR & ESMS.

Workup

  1. customThe reaction was quenched with methanol
  2. washThe ethyl acetate solution was washed twice with saturated sodium bicarbonate solution, once with water, once with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvents were removed under reduced pressure
  5. customthe residue purified by flash chromatography (7% methanol in dichloromethane)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8add7af64a9d425493d309b6ccb2492b
Source dataset
uspto-grants-2011_01
Patent number
US07875733B2

Reaction notes

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