Benzene → Methyl 2-acetyl-6-[(4,6-dimethoxytriazin-2-yl)oxy]benzoate

HRID 1464202Notes

Reaction equation

HRID 1464202 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([OH:14])[C:9]=1[C:10]([O:12][CH3:13])=[O:11])(=[O:3])[CH3:2].[H-].[Na+].C1C=CC=CC=1.Cl[N:24]1[N:29]=[C:28]([O:30][CH3:31])[CH:27]=[C:26]([O:32][CH3:33])[NH:25]1>O>[C:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([O:14][N:24]2[N:25]=[C:26]([O:32][CH3:33])[CH:27]=[C:28]([O:30][CH3:31])[NH:29]2)[C:9]=1[C:10]([O:12][CH3:13])=[O:11])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 241BenzeneHCID 24758Sodium hydrideHCID 590318Methyl 2-acetyl-6-hydroxybenzoateHCID 221477162-Chloro-4,6-dimethoxy-triazine

Product 1

HCID 19089388Methyl 2-acetyl-6-[(4,6-dimethoxytriazin-2-yl)oxy]benzoateYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1.0 g of methyl 6-acetylsalicylate was added to a suspension solution of 0.23 g of sodium hydride and 30 ml of benzene, and the resultant mixture was stirred for 10 minutes at room temperature. 0.95 g of 2-chloro-4,6-dimethoxytriazine was added to the resultant mixture, and the mixture was stirred for one day and one night at room temperature. After completing the reaction, the reaction liquor was poured into water, and was extracted with ethyl acetate. The extracted product was washed with water, dried and concentrated to obtain a crystal. The product thus obtained was purified by column chromatography to obtain 1.15 g of the aimed compound (melting point=151° to 156° C.) at a yield of 67%.

Workup

  1. customthe reaction
  2. extractionwas extracted with ethyl acetate
  3. washThe extracted product was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customto obtain a crystal
  7. customThe product thus obtained
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-e0921ef0ecdc4b1fab47b8ca7c638b0d
Source dataset
uspto-grants-1994_04
Patent number
US05302739

Reaction notes

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