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

HRID 1386818Notes

Reaction equation

HRID 1386818 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7]I)=[CH:5][N:6]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:15][N:16]1[C:21](=[N:22][N+:23]([O-:25])=[O:24])[NH:20][CH2:19][O:18][CH2:17]1>CN(C)C=O>[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:20]2[CH2:19][O:18][CH2:17][N:16]([CH3:15])[C:21]2=[N:22][N+:23]([O-:25])=[O:24])=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 98166342-Chloro-5-(iodomethyl)thiazoleHCID 136277959153719-38-1

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2.0 g of 2-chloro-5-iodomethyl-thiazole, 20 ml of dimethylformamide, 2.66 g of potassium carbonate and 1.23 g of 3-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine is stirred for 16 hours at 50° C., cooled to room temperature and filtered; the filtrate is concentrated to dryness by evaporation. The residue is purified by column chromatography on silica gel using dichloromethane/methanol (9:1), yielding the title compound having a melting point of 132-134° C.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. concentrationthe filtrate is concentrated to dryness by evaporation
  4. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-528c66170e6b4e0f88773a99109ec934
Source dataset
uspto-grants-2001_07
Patent number
US06265585B1

Reaction notes

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