Dimethylamine → N-(2-chloro-5-thiazolylmethyl)-N',N'-dimethyl-N"-nitroguanidine

HRID 1275362Notes

Reaction equation

HRID 1275362 reaction equation
[CH3:1][NH:2][CH3:3].[Cl:4][C:5]1[S:6][C:7]([CH2:10][NH:11][C:12](=[N:15][N+:16]([O-:18])=[O:17])SC)=[CH:8][N:9]=1>C(#N)C>[Cl:4][C:5]1[S:6][C:7]([CH2:10][NH:11][C:12]([N:2]([CH3:3])[CH3:1])=[N:15][N+:16]([O-:18])=[O:17])=[CH:8][N:9]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 136331499N-(2-chloro-5-thiazolylmethyl)-S-methyl-N'-nitroisothiourea

Product 1

HCID 136218199N-(2-chloro-5-thiazolylmethyl)-N',N'-dimethyl-N"-nitroguanidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

252 mg of a 50% aqueous dimethylamine solution was dropwise added to a mixture consisting of 600 mg N-(2-chloro-5-thiazolylmethyl)-S-methyl-N'-nitroisothiourea and 20 ml acetonitrile at room temperature. After stirring at room temperature for 2 hours the reaction mixture was concentrated and 20 ml of ethanol was added to the residue, followed by stirring thoroughly. The resultant crystals were collected by filtration and dried to afford 350 mg of N-(2-chloro-5-thiazolylmethyl)-N',N'-dimethyl-N"-nitroguanidine (compound No.17) as a white powder. The mothor liquor after the filtration was concentrated and 5 ml of ethanol was added, followed by stirring thoroughly, then the resultant crystals were collected by filtration and dried to give additional 120 mg of compound No.17 (mp 154-159° C.). Recrystallization of this product from acetonitrile afforded a product having a melting point of 164-166° C.

Workup

  1. concentrationwas concentrated
  2. addition20 ml of ethanol was added to the residue
  3. stirringby stirring thoroughly
  4. filtrationThe resultant crystals were collected by filtration
  5. customdried

Sources & evidence

ORD record
ord-100b6eeac317443788a2e54e3992c991
Source dataset
uspto-grants-2000_12
Patent number
US06160126

Reaction notes

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