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

HRID 1034184Notes

Reaction equation

HRID 1034184 reaction equation
[CH3:1][N:2]1[C:6](SC)=[C:5]([N+:9]([O-:11])=[O:10])[S:4][C:3]1=[O:12].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][NH:21][CH3:22])=[CH:16][N:15]=1>C(O)C>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][N:21]([C:6]2[N:2]([CH3:1])[C:3](=[O:12])[S:4][C:5]=2[N+:9]([O-:11])=[O:10])[CH3:22])=[CH:16][N:15]=1

Participants

4

Reactant 2

HCID 110948836-Chloro-N-methyl-3-pyridinemethanamineHCID 150304623-Methyl-4-methylthio-5-nitro-2-thiazolone

Product 1

HCID 150304634-[N-(2-chloro-5-pyridylmethyl)-N-methylamino]-3-methyl-5-nitro-2-thiazoloneYield 91.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture consisting of 3-methyl-4-methylthio-5-nitro-2-thiazolone (1.0 g), N-(2-chloro-5-pyridylmethyl)-N-methylamine (0.9 g) and ethanol (30 ml) was heat-refluxed for five hours and then cooled to room temperature to obtain the desired 4-[N-(2-chloro-5-pyridylmethyl)-N-methylamino]-3-methyl-5-nitro-2-thiazolone (1.4 g) having a melting point in the range from 147° to 148° C. in a crystal form.

Workup

  1. temperaturewas heat-refluxed for five hours

Sources & evidence

ORD record
ord-87d158fca10f4a91844c1c6abff059e0
Source dataset
uspto-grants-1994_05
Patent number
US05314897

Reaction notes

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