Potassium Carbonate → 5-(2-Chloropyrid-5-ylmethyl)-3-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine

HRID 842609Notes

Reaction equation

HRID 842609 reaction equation
[CH3:1][N:2]1[C:7](=[N:8][N+:9]([O-:11])=[O:10])[NH:6][CH2:5][O:4][CH2:3]1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19]Cl)=[CH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][N:6]2[CH2:5][O:4][CH2:3][N:2]([CH3:1])[C:7]2=[N:8][N+:9]([O-:11])=[O:10])=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1554792-Chloro-5-(chloromethyl)pyridineHCID 136277959153719-38-1

Product 1

HCID 543833745-(2-Chloropyrid-5-ylmethyl)-3-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.44 g of 3-methyl-4-nitroiminoperhydro-1,3,5-oxadiazine, 2.2 g of 2-chloro-5-chloromethylpyridine, 3.7 g of potassium carbonate and 20 ml of N,N-dime-thylformamide is heated for 4 hours at 50° and filtered, the filtrate is evaporated in vacuo on a rotary evaporator, and the residue is purified by chromatography [silica gel; dichloro-methane/methanol (95:5)]. This gives the tide compound which melts at 116 to 118°.

Workup

  1. temperatureis heated for 4 hours at 50°
  2. filtrationfiltered
  3. customthe filtrate is evaporated in vacuo on a rotary evaporator
  4. customthe residue is purified by chromatography [silica gel; dichloro-methane/methanol (95:5)]
  5. customThis gives the tide compound which melts at 116 to 118°

Sources & evidence

ORD record
ord-a4a73ec6d4284379b68405a03bee4311
Source dataset
uspto-grants-2002_04
Patent number
US06376487B1

Reaction notes

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