Dimethylformamide → HCID 59479923, compound

HRID 1803027Notes

Reaction equation

HRID 1803027 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.[OH:12][C:13]1[CH:23]=[CH:22][C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH2:20]([O:19][C:17](=[O:18])[C:16]1[CH:22]=[CH:23][C:13]([O:12][CH2:2][C:3]2[C:8]([CH3:9])=[N:7][C:6]([CH3:10])=[C:5]([CH3:11])[N:4]=2)=[CH:14][CH:15]=1)[CH3:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8434EthylparabenHCID 11430Potassium CarbonateHCID 135849922-(Bromomethyl)-3,5,6-trimethylpyrazine

Product 1

HCID 59479923HCID 59479923, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

Adding 2-bromomethyl-3,5,6-trimethylpyrazine (0.86 g, 0.0040 mol), ethyl p-hydroxybenzoate (0.948 g, 0.0057 mol), anhydrous potassium carbonate (1.38 g, 0.0103 mol), and DMF (60 mL) into a 100 mL three-necked bottle in turn, heating to 85° C. with oil bath, stirring to react for 12 hours, TLC [V(cyclohexane):V(ethyl acetate)=3:1 as developing agent] detecting shows that reaction is complete, (Rf of raw material=0.5, Rf of product=0.4), and the reaction solution appears yellow, filtering to obtain yellow 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(cyclohexane):V(ethyl acetate)=3:1, collecting product, rotating distilling to obtain light yellow solid, recrystallizing with anhydrous alcohol to obtain 0.76 g 4-((3,5,6-trimethylpyrazine-2-yl)methoxyl)benzoic acid ethyl ester, a yield is 63.3%, m.p. 75.0-75.7° C.

Workup

  1. customto react for 12 hours
  2. filtrationfiltering
  3. customto obtain yellow 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
  9. distillationrotating distilling
  10. customto obtain light yellow solid
  11. customrecrystallizing with anhydrous alcohol

Sources & evidence

ORD record
ord-3ccaa9db1dca4244a14f568342a35594
Source dataset
uspto-grants-2013_01
Patent number
US08350033B2

Reaction notes

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