Sodium hydride → HCID 86590010, compound

HRID 1883613Notes

Reaction equation

HRID 1883613 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:12][C:11](=[N:13][N+:14]([O-:16])=[O:15])[NH:10][C@H:9]2[CH3:17])=[CH:4][CH:3]=1.[H-].[Na+].[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27]Cl)=[CH:23][N:22]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[O:12][C:11](=[N:13][N+:14]([O-:16])=[O:15])[N:10]([CH2:27][C:24]3[CH:25]=[CH:26][C:21]([Cl:20])=[N:22][CH:23]=3)[C@H:9]2[CH3:17])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 136377646HCID 136377646, compound

Product 1

HCID 86590010HCID 86590010, compoundYield 33.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.0 g of trans-5-(4-chlorophenyl)-4-methyl-2-nitroiminooxazolidine obtained in Example 1 and 0.2 g of 60% sodium hydride were added into 20 ml of DMF. 0.7 g of 2-chloro-5-chloromethylpyridine was added gradually to the mixture with stirring on cooling. Then, the mixture was further stirred for 6 hours at 70° C., followed by pouring the reaction mixture into ice water. The solution was extracted with ethyl acetate, and the organic layer was dried and then condensed under reduced pressure. The oily product obtained was purified by column chromatography to give 0.5 g of the title compound.

Workup

  1. temperatureon cooling
  2. stirringThen, the mixture was further stirred for 6 hours at 70° C.
  3. extractionThe solution was extracted with ethyl acetate
  4. customthe organic layer was dried
  5. customcondensed under reduced pressure
  6. customThe oily product obtained
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-5b3fa14768364fdb8e645a211ab8949f
Source dataset
uspto-grants-2004_07
Patent number
US06762200B2

Reaction notes

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