Potassium Carbonate → n-(3-((2-Chlorothiazol-5-yl)methyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene)nitramide

HRID 635519Notes

Reaction equation

HRID 635519 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[S:14][C:15]([CH2:18]Cl)=[CH:16][N:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[Cl:12][C:13]1[S:14][C:15]([CH2:18][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:16][N:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27631792-Chloro-5-chloromethylthiazoleHCID 136277959153719-38-1

Product 1

HCID 107646n-(3-((2-Chlorothiazol-5-yl)methyl)-5-methyl-1,3,5-oxadiazinan-4-ylidene)nitramideYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.62 g of 3-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine, 2.44 g of 2-chloro-5-chloromethyl-thiazole, 4.2 g of potassium carbonate and 25 ml of N,N-dimethylformamide is heated for 5 h at 60° and then filtered. The filtrate is evaporated in vacuo on a rotary evaporator, and the residue is purified by chromatography [silica gel; dichloromethane/methanol (95:5)]. This gives the title compound, which melts at 132-134°, in a yield of 67%.

Workup

  1. temperatureis heated for 5 h at 60°
  2. filtrationfiltered
  3. customThe filtrate is evaporated in vacuo on a rotary evaporator
  4. customthe residue is purified by chromatography [silica gel; dichloromethane/methanol (95:5)]

Sources & evidence

ORD record
ord-74a154dd504142c680e804c5c12dac8b
Source dataset
uspto-grants-2001_02
Patent number
US06187927B1

Reaction notes

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