1,1'-(Chlorophenylmethylene)bis(4-methoxybenzene) → HCID 90411616, compound

HRID 1754599Notes

Reaction equation

HRID 1754599 reaction equation
[C:1](Cl)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:10]1[CH:17]=[CH:16][C:13]([O:14][CH3:15])=[CH:12][CH:11]=1)[C:2]1[CH:9]=[CH:8][C:5]([O:6][CH3:7])=[CH:4][CH:3]=1.[O:25]([C@H:33]([CH3:56])[C@H:34]([CH2:37][N:38]1[CH:46]=[N:45][C:44]2[C:39]1=[N:40][CH:41]=[N:42][C:43]=2[NH:47][C:48](=[O:55])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[CH2:35][OH:36])[Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>N1C=CC=CC=1>[O:25]([C@H:33]([CH3:56])[C@H:34]([CH2:37][N:38]1[CH:46]=[N:45][C:44]2[C:39]1=[N:40][CH:41]=[N:42][C:43]=2[NH:47][C:48](=[O:55])[C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[CH2:35][O:36][C:1]([C:2]1[CH:9]=[CH:8][C:5]([O:6][CH3:7])=[CH:4][CH:3]=1)([C:10]1[CH:17]=[CH:16][C:13]([O:14][CH3:15])=[CH:12][CH:11]=1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[Si:26]([C:29]([CH3:30])([CH3:31])[CH3:32])([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 968311,1'-(Chlorophenylmethylene)bis(4-methoxybenzene)HCID 90411608HCID 90411608, compound

Product 1

HCID 90411616HCID 90411616, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

DMTCl (0.8 g. 2.37 mmol) was added in one portion to a stirred solution of 12 (0.82 g, 1.8 mmol) in 20 ml of anhydrous pyridine. The reaction was kept at room temperature for 20 hrs, concentrated and partitioned between ethyl acetate and 10% citric acid. The organic phase was washed with saturated NaCl, dried over Na2SO4 and concentrated. The resultant crude product was chromatographed on silica eluting with 50% ethyl acetate in hexane. Concentration of the pure product fractions afforded 1.2 g (88%) of 13 as a white amorphous solid. 1H NMR (DMSO-d6): δ 11.12 (s, 1H), 8.70 (s, 1H), 8.38 (s, 1H), 8.05 (d, J=8.7 Hz, 2H), 7.65 (m, 1H), 7.55 (t, J=7.5 Hz. 2H), 7.18 (m, 5H), 7.04 (t, J=8.7, 4H), 6.77 (m, 4H), 4.36 (m, 1H), 4.24 (m, 1H), 4.02 (m, 1H), 3.60 (s, 6H), 3.12 (m, 1H), 2.95 (m, 1H), 2.39 (m, 1H), 1.14 (d, J=6.6 Hz, 3H), 0.74 (s, 9H), 0.00 (s, 3H), −0.10 (s, 3H).

Workup

  1. concentrationconcentrated
  2. custompartitioned between ethyl acetate and 10% citric acid
  3. washThe organic phase was washed with saturated NaCl
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe resultant crude product was chromatographed on silica eluting with 50% ethyl acetate in hexane

Sources & evidence

ORD record
ord-d349c10c5447488a98aad5f0e13e3c52
Source dataset
uspto-grants-2015_10
Patent number
US09169256B2

Reaction notes

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