Hydrochloric Acid → HCID 19081372, compound

HRID 963207Notes

Reaction equation

HRID 963207 reaction equation
[Cl:1][C:2]1[CH:7]=[N:6][NH:5][C:4](=[O:8])[C:3]=1[CH2:9][O:10][CH3:11].[H-].[Na+].[CH3:14]I.Cl>O.CN(C)C=O>[Cl:1][C:2]1[CH:7]=[N:6][N:5]([CH3:14])[C:4](=[O:8])[C:3]=1[CH2:9][O:10][CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 19081368HCID 19081368, compound

Product 1

HCID 19081372HCID 19081372, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Into 22 ml of an N,N-dimethylformamide solution of 2.17 g of 5-chloro-4-methoxymethylpyridazin-3-(2H)-one prepared in the above step (3), 0.55 g of sodium hydride (containing 40% of mineral oil) was added at room temperature. After the addition, the mixture was stirred for 30 minutes. Then, 2.12 g of methyl iodide was dropwise added thereto at a temperature of not higher than 20° C. After completion of the dropwise addition, the mixture was stirred at room temperature for one hour. After completion of the reaction, 70 ml of water and 4 ml of 10% hydrochloric acid were added to the reaction mixture, and the mixture was extracted with 70 ml of benzene. The benzene layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was subjected to silica gel column chromatography, and from a fraction of n-hexane:ethyl acetate=3:1, 1.53 g of 5-chloro-2-methyl-4-methoxymethylpyridazin-3-(2H)-one having a melting point of from 47 to 49° C., was obtained.

Workup

  1. additionwas added at room temperature
  2. additionAfter the addition
  3. customhigher than 20° C
  4. additionAfter completion of the dropwise addition
  5. stirringthe mixture was stirred at room temperature for one hour
  6. additionwere added to the reaction mixture
  7. extractionthe mixture was extracted with 70 ml of benzene
  8. dry with materialThe benzene layer was dried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-159215a7e64540868612d8e3a3baad84
Source dataset
uspto-grants-1998_06
Patent number
US05763439

Reaction notes

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