Potassium Carbonate → HCID 18518222, compound

HRID 1368928Notes

Reaction equation

HRID 1368928 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[CH:13]=[CH:14]/[CH:15]=[CH:16]/[C:17]([NH:19][C:20]2[C:25]([NH:26][C:27](=[O:44])/[CH:28]=[CH:29]/[CH:30]=[CH:31]/[C:32]3[CH:37]=[C:36]([O:38][CH3:39])[C:35]([O:40][CH3:41])=[C:34]([O:42][CH3:43])[CH:33]=3)=[CH:24][CH:23]=[CH:22][C:21]=2[O:45]C(=O)/C=C/C=C/C2C=C(OC)C(OC)=C(OC)C=2)=[O:18])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(=O)([O-])[O-].[K+].[K+]>CO.O1CCCC1>[CH3:12][O:11][C:7]1[CH:6]=[C:5](/[CH:13]=[CH:14]/[CH:15]=[CH:16]/[C:17]([NH:19][C:20]2[C:25]([NH:26][C:27](=[O:44])/[CH:28]=[CH:29]/[CH:30]=[CH:31]/[C:32]3[CH:33]=[C:34]([O:42][CH3:43])[C:35]([O:40][CH3:41])=[C:36]([O:38][CH3:39])[CH:37]=3)=[CH:24][CH:23]=[CH:22][C:21]=2[OH:45])=[O:18])[CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 18518197HCID 18518197, compound

Product 1

HCID 18518222HCID 18518222, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 196 mg (0.23 mmol) of N,N′,O-tri[5-(3,4,5-trimethoxyphenyl)penta-(2E,4E)-dienoyl]-2,3-diaminophenol synthesized by the process described above in anhydrous methanol-tetrahydrofuran (3 ml-3 ml) was cooled in an ice bath. To the solution was added 19 mg (0.14 mmol) of potassium carbonate. The ice bath was removed, and the mixture was stirred for 1 hour at room temperature. Added to the reaction mixture were 0.5 ml of 1N hydrochloric acid and 5 ml of a saturated saline solution to conduct extraction with chloroform. An organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil (515 mg) was purified by column chromatography on silica gel, thereby obtaining 126 mg (yield: 90%) of crude crystals of the title compound. The crude crystals thus obtained were recrystallized from ethanol-ether, thereby obtaining a pale yellow crystalline powder.

Workup

  1. temperaturewas cooled in an ice bath
  2. customThe ice bath was removed
  3. additionAdded to the reaction mixture
  4. extractionextraction with chloroform
  5. dry with materialAn organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant crude oil (515 mg) was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-be59d30587054220a59448dd20637a4b
Source dataset
uspto-grants-2003_06
Patent number
US06576642B2

Reaction notes

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