2-Chloro-5-aminomethylthiazole → 1-(1-Chloroethoxycarbonyl)-3-(2-chloro-5-thiazolylmethyl)-1-methyl-2-nitroguanidine

HRID 1657032Notes

Reaction equation

[Cl:1][CH:2]([O:4][C:5]([N:7]([CH3:15])[C:8](=[N:11][N+:12]([O-:14])=[O:13])SC)=[O:6])[CH3:3].[Cl:16][C:17]1[S:18][C:19]([CH2:22][NH2:23])=[CH:20][N:21]=1>C(Cl)(Cl)Cl>[Cl:1][CH:2]([O:4][C:5]([N:7]([CH3:15])[C:8]([NH:23][CH2:22][C:19]1[S:18][C:17]([Cl:16])=[N:21][CH:20]=1)=[N:11][N+:12]([O-:14])=[O:13])=[O:6])[CH3:3]

Participants

Conditions

Temperature: -20 °C

Procedure

To a stirred solution of N-(1-chloroethoxycarbonyl)-S,N-dimethyl-N'-nitroisothiourea (6.50 g) in CHCl3 (15 ml) was added a solution of 2-chloro-5-thiazolylmethylamine (3.78 g) in CHCl3 (5 ml) dropwise below -20° C. over 20 minutes. After stirring at -20° C. for 30 minutes, insolubles were removed by filtration and the filtrate was concentrated in vacuo. The residue was applied to column chromatography on silica gel. The column was eluted with hexane-AcOEt (1:1) to afford 3.50 g of 1-(1-chloroethoxycarbonyl)-3-(2-chloro-5-thiazolylmethyl)-1-methyl-2-nitroguanidine (Compound No. 12) as an orange oil.

Workup

custominsolubles were removed by filtration
concentrationthe filtrate was concentrated in vacuo
washThe column was eluted with hexane-AcOEt (1:1)

Sources & evidence

ORD record: ord-aed818bb104d487aaca0b5a48d7700ef
Source dataset: uspto-grants-1993_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05256679

Reaction notes

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