1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 137252535, compound

HRID 2191021Notes

Reaction equation

HRID 2191021 reaction equation
[OH:1][CH:2]1[CH:6]([CH2:7][OH:8])[O:5][CH:4]([N:9]2[CH:17]=[N:16][C:15]3[C:14](=[O:18])[NH:13][C:12]([NH:19][C:20](=[O:24])[CH:21]([CH3:23])[CH3:22])=[N:11][C:10]2=3)[CH:3]1[O:25][CH3:26].[C:27](Cl)(C1C=CC=CC=1)([C:36]1[CH:43]=[CH:42][C:39]([O:40][CH3:41])=[CH:38][CH:37]=1)[C:28]1[CH:35]=[CH:34][C:31]([O:32][CH3:33])=[CH:30][CH:29]=1>N1C=CC=CC=1>[CH3:41][O:40][C:39]1[CH:38]=[CH:37][C:36]([CH:27]([C:28]2[CH:29]=[CH:30][C:31]([O:32][CH3:33])=[CH:34][CH:35]=2)[O:8][CH:7]([C:28]2[CH:35]=[CH:34][CH:31]=[CH:30][CH:29]=2)[CH:6]2[O:5][CH:4]([N:9]3[CH:17]=[N:16][C:15]4[C:14](=[O:18])[NH:13][C:12]([NH:19][C:20](=[O:24])[CH:21]([CH3:22])[CH3:23])=[N:11][C:10]3=4)[CH:3]([O:25][CH3:26])[CH:2]2[OH:1])=[CH:43][CH:42]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 136351472HCID 136351472, compound

Product 1

HCID 137252535HCID 137252535, compoundYield 41.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Compound 16.2 (6.18 g, 17.19 mmol) was dissolved in 15 mL anhydrous pyridine, and treated with DMTCl (6.4 g, 18.91 mmol). The mixture was stirred for 12 h and poured on to 200 mL ice-water, filtered, and the solid was washed with 2×100 mL water. The solid was redissolved in 200 mL ethyl acetate. The organic layer was washed with 3×100 mL water, dried over MgSO4, filtered, and concentrated down under reduced pressure. The residue was subjected to a silica gel column chromatography to yield product 16.3 (2.6 g, 23% yield).

Workup

  1. filtrationfiltered
  2. washthe solid was washed with 2×100 mL water
  3. dissolutionThe solid was redissolved in 200 mL ethyl acetate
  4. washThe organic layer was washed with 3×100 mL water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated down under reduced pressure

Sources & evidence

ORD record
ord-2d958fc80a0e4036b0f3899c9ad55e47
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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