Acetonitrile → 4-[N-(2-chloro-5-pyridylmethyl)-N-methylamino]-3-methyl-5-nitro-2-thiazolone

HRID 1587727Notes

Reaction equation

HRID 1587727 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([NH:15][CH3:16])=[CH:11][N+:12]([O-:14])=[O:13])=[CH:4][N:3]=1.Cl[C:18]([S:20]Cl)=[O:19].[C:22](#N)C>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([C:10]2[N:15]([CH3:16])[C:18](=[O:19])[S:20][C:11]=2[N+:12]([O-:14])=[O:13])[CH3:22])=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 75990(Chlorothio)formyl chlorideHCID 43256191,1-Ethenediamine, N-[(6-chloro-3-pyridinyl)methyl]-N'-methyl-2-nitro-

Product 1

HCID 150304634-[N-(2-chloro-5-pyridylmethyl)-N-methylamino]-3-methyl-5-nitro-2-thiazolone

Procedure

To a mixture of 1-(2-chloro-5-pyridylmethylamino)-1-methylamino-2-nitroethylene (3.0 g) and acetonitrile (30 ml) was added slowly and dropwise chlorocarbonylsulfenyl chloride (1.8 g) at 10° to 20° C. After an overnight stirring, the solvent was distilled off from the reaction liquid under reduced pressure and the thus obtained residue was refined with column chromatography (eluant: ethanol/chloroform=1/10) to obtain the desired 4-[N-(2-chloro-5-pyridylmethyl)-N-methylamino]-3-methyl-5-nitro-2-thiazolone (1.0 g) having a melting point in the range from 147° to 148° C.

Workup

  1. additionwas added slowly
  2. customat 10° to 20° C
  3. distillationthe solvent was distilled off from the reaction liquid under reduced pressure

Sources & evidence

ORD record
ord-01ccc3f012d04ba48b3c65416b349579
Source dataset
uspto-grants-1993_06
Patent number
US05219869

Reaction notes

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