Dimethyl Sulfoxide → Benzaldehyde, 2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]-

HRID 344568

Reaction equation

HRID 344568 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.[CH:12]1[CH:17]=[C:16]([CH:18]=[O:19])[C:15]([OH:20])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[K+].[K+].CS(C)=O>O>[CH3:11][O:10][C:4]1[CH:5]=[C:6]([O:8][CH3:9])[N:7]=[C:2]([O:20][C:15]2[CH:14]=[CH:13][CH:12]=[CH:17][C:16]=2[CH:18]=[O:19])[N:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6998SalicylaldehydeHCID 11430Potassium CarbonateHCID 51523232-Chloro-4,6-dimethoxypyrimidine

Product 1

HCID 820623Benzaldehyde, 2-[(4,6-dimethoxy-2-pyrimidinyl)oxy]-Yield 99.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A 500-ml four-necked flask was charged with a mixture of 105 g (0.6 mole) of 2-chloro-4,6-dimethoxypyrimidine, 79.4 g (0.65 mole) of salicylic aldehyde, 48.3 g (0.35 mole) of potassium carbonate and 450 ml of dimethylsulfoxide. The mixture was gradually heated, and stirred at 120° C. for 3 hours. After the reaction mixture was cooled, it was poured into 2 l of water. Through the procedures of benzene extraction, washing with water, drying over anhydrous sodium sulfate and concentration, 156 g of the target product were obtained as a crude oil. It was purified further by silica gel chromatography to obtain 117.1 g of white crystals (yield: 75.0%). Melting point: 76.0° about 76.5° C.

Workup

  1. temperatureThe mixture was gradually heated
  2. temperatureAfter the reaction mixture was cooled
  3. extractionThrough the procedures of benzene extraction
  4. washwashing with water
  5. dry with materialdrying over anhydrous sodium sulfate and concentration

Sources & evidence

ORD record
ord-e1c7c33a9db2439b820966d43db03769
Source dataset
uspto-grants-1991_10
Patent number
US05053070

Linked notes

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