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

HRID 1939603Notes

Reaction equation

HRID 1939603 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 ! 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-6d2049a072db4916a1a4172a611e6727
Source dataset
uspto-grants-1997_12
Patent number
US05696256

Reaction notes

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