Methanol → HCID 21841985, compound

HRID 1737218Notes

Reaction equation

HRID 1737218 reaction equation
Cl[C:2]1[N:6]([C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])[C:5](=[O:17])[N:4]([CH3:18])[N:3]=1.[CH3:19][OH:20].C[O-].[Na+].[Cl-].[NH4+]>COCCOC>[CH3:19][O:20][C:2]1[N:6]([C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])[C:5](=[O:17])[N:4]([CH3:18])[N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 25517Ammonium ChlorideHCID 10942334Sodium MethoxideHCID 21841991HCID 21841991, compound

Product 1

HCID 21841985HCID 21841985, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution containing 10 g of the title compound of Step B dissolved in 110 mL of 1,2-dimethoxyethane and 50 mL of methanol under a nitrogen atmosphere was added dropwise 21.4 L of 30% sodium methoxide. The reaction mixture was stirred at room temperature for approximately 24 h, then heated to 40° C. for 1 h, then heated to 50° C. for 4 h, and finally cooled to 0° C. The reaction was poured into a saturated aqueous solution of ammonium chloride. The organic layer was separated and washed with saturated aqueous ammonium chloride. The organic layer was then dried over magnesium sulfate and filtered, and the filtrate was then evaporated to obtain 7.74 g of the title compound of Step C as a white solid.

Workup

  1. temperatureheated to 40° C. for 1 h
  2. temperatureheated to 50° C. for 4 h
  3. temperaturefinally cooled to 0° C
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous ammonium chloride
  6. dry with materialThe organic layer was then dried over magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate was then evaporated

Sources & evidence

ORD record
ord-620aface86f240088e715fd0357c0491
Source dataset
uspto-grants-1999_10
Patent number
US05962436

Reaction notes

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