Dimethylformamide → HCID 14648785, compound

HRID 1073466Notes

Reaction equation

HRID 1073466 reaction equation
[OH:1][C:2]1[C:3]([C:8]([O:10][N:11]=[C:12]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH2:15][CH3:16])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.CS([C:25]1[N:30]=[C:29]([O:31][CH3:32])[CH:28]=[C:27]([O:33][CH3:34])[N:26]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:34][O:33][C:27]1[CH:28]=[C:29]([O:31][CH3:32])[N:30]=[C:25]([O:1][C:2]2[C:3]([C:8]([O:10][N:11]=[C:12]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:13][CH2:14][CH2:15][CH3:16])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=2)[N:26]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 14648780HCID 14648780, compound

Product 1

HCID 14648785HCID 14648785, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 6.3 g of 5-nonanylidenamino 3-hydroxypicolinate, 2.5 g of 2-methylsulfonyl-4,6-dimethoxypyrimidine and 3.9 g of anhydrous potassium carbonate, 50 ml of N,N-dimethylformamide was added, and the mixture was stirred at 100° C. for 2 hours. After cooling, the reaction solution was poured into water and extracted with ethyl ether. The organic layer was further washed with water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue thereby obtained was purified by silica gel column chromatography by using as a developing solvent a mixture of hexane/ethyl ether to obtain 5.2 g of the above identified compound as slightly yellow transparent viscous liquid.

Workup

  1. additionwas added
  2. temperatureAfter cooling
  3. extractionextracted with ethyl ether
  4. washThe organic layer was further washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue thereby obtained
  8. customwas purified by silica gel column chromatography
  9. additiona mixture of hexane/ethyl ether
  10. customto obtain 5.2 g of the

Sources & evidence

ORD record
ord-d93ddb707cb240b79dfb27328e5ad99a
Source dataset
uspto-grants-1990_11
Patent number
US04969949

Reaction notes

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