Potassium Carbonate → HCID 12135696, compound

HRID 1582794Notes

Reaction equation

HRID 1582794 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].F[C:16]1[CH:17]=[C:18]([CH:48]=[CH:49][CH:50]=1)[O:19][C:20]1[CH:21]=[C:22]([CH:45]=[CH:46][CH:47]=1)[O:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][C:38]3[CH:43]=[CH:42][CH:41]=[C:40](F)[CH:39]=3)[CH:32]=2)[CH:25]=1.[NH2:51][C:52]1[CH:53]=[C:54]([CH:133]=[CH:134][CH:135]=1)[O:55]C1C=C(C=CC=1)OC1C=C(C2C(OC3C=CC=C(OC4C=CC=C(F)C=4)C=3)=CC=CC=2OC2C=CC=C(OC3C=CC=C(OC4C=CC=C(F)C=4)C=3)C=2C2C=CC=C(OC3C=CC=C(OC4C=CC=C(N)C=4)C=3)C=2)C=CC=1>CN1C(=O)N(C)CC1>[NH2:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][CH:7]=1)[O:8][C:16]1[CH:17]=[C:18]([CH:48]=[CH:49][CH:50]=1)[O:19][C:20]1[CH:21]=[C:22]([CH:45]=[CH:46][CH:47]=1)[O:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([O:37][C:38]3[CH:43]=[CH:42][CH:41]=[C:40]([O:55][C:54]4[CH:133]=[CH:134][CH:135]=[C:52]([NH2:51])[CH:53]=4)[CH:39]=3)[CH:32]=2)[CH:25]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 115683-AminophenolHCID 12135695HCID 12135695, compoundHCID 86588087HCID 86588087, compound

Product 1

HCID 12135696HCID 12135696, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 66611,3-Dimethyl-2-imidazolidinoneSolvent

Conditions

Temperature
210 °C

Procedure

In a nitrogen atmosphere, 1 g (9 mmole) of m-aminophenol was dissolved in 20 ml of DMI, and 2 g (15 mmole) of potassium carbonate was added, followed by stirring for 30 minutes. Then, 1 g (2 mmole) of 1,3-bis(3-(3-fluorophenoxy)phenoxy)benzene was added, and the mixture was stirred for 14 hours under heating at 210° C. The progress of the reaction was confirmed by HPLC. When the intermediate product, 3-(3-(3-aminophenoxy)phenoxy)phenyl-3-(3-(3-fluorophenoxy)phenoxy)phenyl ether almost disappeared, the reaction was terminated. Then, liquid separation was carried out in the same manner as in Example 2 to obtain an organic phase, and the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to obtain 1.1 g (1.6 mmole, yield: 86%, purity (HPLC): 98%) of 1,3-bis(3-(3-(3-aminophenoxy)phenoxy)phenoxy)benzene as a yellow oily product. The structure and the properties of the compound are as follows.

Workup

  1. stirringthe mixture was stirred for 14 hours
  2. customthe reaction was terminated
  3. customThen, liquid separation
  4. customto obtain an organic phase
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-eef58b650d96402d90945f6b5d6dfc9b
Source dataset
uspto-grants-2004_05
Patent number
US06737503B2

Reaction notes

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