Dimethylformamide → HCID 59479924, compound

HRID 1803029Notes

Reaction equation

HRID 1803029 reaction equation
Br[CH2:2][C:3]1[C:8]([CH3:9])=[N:7][C:6]([CH3:10])=[C:5]([CH3:11])[N:4]=1.[C:12]([O:23][CH3:24])(=[O:22])[C:13]1[CH:21]=[CH:20][C:18]([OH:19])=[C:15]([O:16][CH3:17])[CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH3:24][O:23][C:12](=[O:22])[C:13]1[CH:21]=[CH:20][C:18]([O:19][CH2:2][C:3]2[C:8]([CH3:9])=[N:7][C:6]([CH3:10])=[C:5]([CH3:11])[N:4]=2)=[C:15]([O:16][CH3:17])[CH:14]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 19844Methyl VanillateHCID 135849922-(Bromomethyl)-3,5,6-trimethylpyrazine

Product 1

HCID 59479924HCID 59479924, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Adding 2-bromomethyl-3,5,6-trimethylpyrazine (0.5 g, 2.33 mmol), methyl vanillate (0.6 g, 3.30 mmol), anhydrous potassium carbonate (1.0 g, 7.25 mmol), and DMF (40 mL) into a 100 mL three-necked bottle in turn, heating to 85° C. with oil bath, stifling to react for 8 hours, TLC [V(cyclohexane):V(ethyl acetate)=3:1 as developing agent] detecting shows that reaction is complete, (Rf of raw material=0.6, Rf of product=0.35), filtering to obtain filtrate, adding 30 mL water, extracting with chloroform (3×30 mL), incorporating the chloroform layer and wishing with water (2×20 mL), drying with anhydrous sodium sulfate, recycling chloroform under reduced pressure to obtain a light yellow oily matter, separating with a silica column, wherein eluant is V(petroleum ether):V(ethyl acetate)=3:1, collecting product, recycling the solution under reduced pressure to obtain solid, 0.51 g white crystalloid of 4-((3,5,6-trimethylpyrazine-2-yl)methoxyl)-3-methoxybenzoic methyl ester, a yield is 69.3%, m.p. 129.8-130.4° C.

Workup

  1. customto react for 8 hours
  2. filtrationfiltering
  3. customto obtain filtrate
  4. extractionextracting with chloroform (3×30 mL)
  5. dry with materialdrying with anhydrous sodium sulfate
  6. customto obtain a light yellow oily matter
  7. customseparating with a silica column, wherein eluant
  8. customV(ethyl acetate)=3:1, collecting product

Sources & evidence

ORD record
ord-b20275a8b01b4d84b235e9b58d7bc02b
Source dataset
uspto-grants-2013_01
Patent number
US08350033B2

Reaction notes

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