Dichloromethane → HCID 70205439, compound

HRID 725827Notes

Reaction equation

HRID 725827 reaction equation
ClCCl.[CH3:4][O:5][C:6]1[CH:7]=[C:8]([CH:12]=[C:13]([O:17][CH3:18])[C:14]=1[O:15][CH3:16])[C:9](Cl)=[O:10].[NH2:19][C:20]1[N:25]2[N:26]=[CH:27][CH:28]=[C:24]2[N:23]=[C:22]([CH2:29][CH2:30][CH:31]([O:33][Si](C)(C)C)[CH3:32])[CH:21]=1.C([O-])(O)=O.[Na+]>N1C=CC=CC=1>[OH:33][CH:31]([CH3:32])[CH2:30][CH2:29][C:22]1[CH:21]=[C:20]([NH:19][C:9](=[O:10])[C:8]2[CH:7]=[C:6]([O:5][CH3:4])[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[CH:12]=2)[N:25]2[N:26]=[CH:27][CH:28]=[C:24]2[N:23]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 516892Sodium BicarbonateHCID 22372113HCID 22372113, compound

Product 1

HCID 70205439HCID 70205439, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A dry dichloromethane solution (5 ml) containing 650 mg of 3,4,5-trimethoxybenzoyl chloride was slowly added dropwise to 5 ml of a pyridine solution containing 520 mg of the crystals obtained in step (7), and stirred at room temperature for 2 hours. After completion of the reaction, a saturated aqueous NaHCO3 solution was added and the reaction mixture was extracted with dichloromethane. The organic layer was collected and washed with a 1N aqueous hydrochloric acid until the pH of the water layer became about 1. The organic layer was allowed to stand for 2 hours, washed with water and a saturated saline solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from dichloromethane-n-hexane to provide 480 mg of the object compound as colorless crystals. Table 2 shows the structure and melting point of the compound obtained.

Workup

  1. customAfter completion of the reaction
  2. extractionthe reaction mixture was extracted with dichloromethane
  3. customThe organic layer was collected
  4. washwashed with a 1N aqueous hydrochloric acid until the pH of the water layer
  5. waitto stand for 2 hours
  6. washwashed with water
  7. dry with materiala saturated saline solution, dried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was recrystallized from dichloromethane-n-hexane

Sources & evidence

ORD record
ord-e99838202452442f8acbd640deded043
Source dataset
uspto-grants-1998_01
Patent number
US05707997

Reaction notes

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