Monomethylamine methanol → N-(2-chloro-5-thiazolylmethyl)-N'-methyl-N"-nitroguanidine

HRID 1275361Notes

Reaction equation

HRID 1275361 reaction equation
CO.[CH3:3][NH2:4].[Cl:5][C:6]1[S:7][C:8]([CH2:11][NH:12][C:13](=[N:16][N+:17]([O-:19])=[O:18])SC)=[CH:9][N:10]=1>C(#N)C>[Cl:5][C:6]1[S:7][C:8]([CH2:11][NH:12][C:13]([NH:4][CH3:3])=[N:16][N+:17]([O-:19])=[O:18])=[CH:9][N:10]=1

Participants

4

Reactant 2

HCID 57454252Monomethylamine methanolHCID 136331499N-(2-chloro-5-thiazolylmethyl)-S-methyl-N'-nitroisothiourea

Product 1

HCID 135779804N-(2-chloro-5-thiazolylmethyl)-N'-methyl-N"-nitroguanidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

349 mg of a 40% methylamine methanol solution was dropwise added to a mixture consisting of 1 g N-(2-chloro-5-thiazolylmethyl)-S-methyl-N'-nitroisothiourea and 30 ml acetonitrile, at room temperature, over 5 minutes. After stirring for 1.5 hours, the resultant white precipitate was collected by filtration and then dried to afford 410 mg of N-(2-chloro-5-thiazolylmethyl)-N'-methyl-N"-nitroguanidine (compound No.14) as a white powder. The mother liquor after the filtration was concentrated, then 20 ml of ethanol was added, followed by stirring thoroughly, and the crystals formed were collected by filtration to obtain additional 330 mg of compound No.14 (mp 172-173° C.). Upon recrystallization from acetonitrile, this product exhibited mp 173-174° C.

Workup

  1. filtrationthe resultant white precipitate was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-b4e715ef19a14c548a36b1db66ec3d12
Source dataset
uspto-grants-2000_12
Patent number
US06160126

Reaction notes

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