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

HRID 1386819Notes

Reaction equation

HRID 1386819 reaction equation
Br[CH2:2][C:3]1[S:7][C:6]([Cl:8])=[N:5][CH:4]=1.CN(C)C=O.[CH3:14][N:15]1[C:20](=[N:21][N+:22]([O-:24])=[O:23])[NH:19][CH2:18][O:17][CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.O>[Cl:8][C:6]1[S:7][C:3]([CH2:2][N:19]2[CH2:18][O:17][CH2:16][N:15]([CH3:14])[C:20]2=[N:21][N+:22]([O-:24])=[O:23])=[CH:4][N:5]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 101305605-Bromomethyl-2-chloro-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 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

3.18 g of 5-bromomethyl-2-chloro-thiazole, 12 ml of dimethylformamide, 1.99 g of 3-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine and 3.79 g of potassium carbonate are combined and the mixture is stirred for 5 hours at 50° C. The mixture is cooled to room temperature and 50 ml of water and 50 ml of dichloromethane are added. The organic phase is separated off and dried over magnesium sulfate; the solvent is evaporated off in vacuo. The residue is purified by column chromatography on silica gel using hexane/ethyl acetate (1:1), yielding the title compound (compound 2-2).

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. customThe organic phase is separated off
  3. dry with materialdried over magnesium sulfate
  4. customthe solvent is evaporated off in vacuo
  5. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-cdcf23eee36945e8a9551518b50797b9
Source dataset
uspto-grants-2001_07
Patent number
US06265585B1

Reaction notes

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