1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 90411741, compound

HRID 1754611Notes

Reaction equation

HRID 1754611 reaction equation
[CH3:1][C:2]1[C:3](=[O:16])[NH:4][C:5](=[O:15])[N:6]([CH2:8][C@H:9]([C@H:12]([OH:14])[CH3:13])[CH2:10][OH:11])[CH:7]=1.[C:17](Cl)([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)([C:26]1[CH:33]=[CH:32][C:29]([O:30][CH3:31])=[CH:28][CH:27]=1)[C:18]1[CH:25]=[CH:24][C:21]([O:22][CH3:23])=[CH:20][CH:19]=1>N1C=CC=CC=1>[CH3:31][O:30][C:29]1[CH:28]=[CH:27][C:26]([C:17]([C:18]2[CH:19]=[CH:20][C:21]([O:22][CH3:23])=[CH:24][CH:25]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[O:11][CH2:10][C@H:9]([CH2:8][N:6]2[CH:7]=[C:2]([CH3:1])[C:3](=[O:16])[NH:4][C:5]2=[O:15])[C@H:12]([OH:14])[CH3:13])=[CH:33][CH:32]=1

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 90411028HCID 90411028, compound

Product 1

HCID 90411741HCID 90411741, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred solution of 33 (0.6 g. 2.6 mmol) in 20 ml of anhydrous pyridine was added 0.9 g (2.66 mmol) of DMTCl. After being stirred at room temperature for 5 hrs the reaction was quenched with methanol (3 ml), concentrated and portioned between 10% citric acid and ethyl acetate. The organic phase was washed with saturated NaCl, dried over Na2SO4 and concentrated in vacuo to a solid foam. The crude product was chromatographed on silica eluting with ethyl acetate to afford 0.95 g (69%) of 34 as an amorphous white solid. 1H NMR (DMSO-d6): δ 11.16 (s, 1H), 7.28 (m, 6H), 7.21 (m, 4H), 6.85 (m, 4H), 4.59 (d, J=5 Hz, 1H), 3.76 (m, 2H), 3.74 (s, 6H), 3.57 (m, 1H), 3.10 (m, 1H), 2.95 (m, 1H), 2.11 (m, 1H), 1.67 (s, 3H), 1.02 (d, J=6.3 Hz, 3H).

Workup

  1. customwas quenched with methanol (3 ml)
  2. concentrationconcentrated
  3. washThe organic phase was washed with saturated NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo to a solid foam
  6. customThe crude product was chromatographed on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-1fc6b9249bed4646a7a99162a2a6be44
Source dataset
uspto-grants-2015_10
Patent number
US09169256B2

Reaction notes

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