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

HRID 1386820Notes

Reaction equation

HRID 1386820 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7]Cl)=[CH:5][N:6]=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:1][C:2]1[S:3][C:4]([CH2:7][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:5][N:6]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 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)nitramide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

2.5 g of 2-chloro-5-chloromethyl-thiazole, 12 ml of dimethylformamide, 2 g of 3-methyl-4-nitroimino-perhydro-1,3,5-oxadiazine and 3.8 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. Purification is carried out 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. customPurification

Sources & evidence

ORD record
ord-d09ecef7da8b409298181102cbf12c60
Source dataset
uspto-grants-2001_07
Patent number
US06265585B1

Reaction notes

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