(2-Chloro-thiazol-5-ylmethyl)-methyl-amine → N-[(2-chloro-5-thiazolyl)methyl]-N-methyl-N'-nitroguanidine

HRID 373794Notes

Reaction equation

HRID 373794 reaction equation
[Cl:1][C:2]1[S:3][C:4]([CH2:7][NH:8][CH3:9])=[CH:5][N:6]=1.CS[C:12](=[NH:17])[NH:13][N+:14]([O-:16])=[O:15]>C(O)C>[Cl:1][C:2]1[S:3][C:4]([CH2:7][N:8]([CH3:9])[C:12]([NH:13][N+:14]([O-:16])=[O:15])=[NH:17])=[CH:5][N:6]=1

Participants

4

Reactant 2

HCID 22450372(2-Chloro-thiazol-5-ylmethyl)-methyl-amineHCID 135927615N-Nitro-S-methylisothiourea

Product 1

HCID 136023519N-[(2-chloro-5-thiazolyl)methyl]-N-methyl-N'-nitroguanidineYield 47.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.50 g of 2-chloro-N-methyl-5-thiazolemethanamine, 1.13 g of S-methyl-N-nitroisothiourea and 6 ml of ethanol was heated under reflux for 6 hours. After cooling, the reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (Solvent: Chloroform/Methanol=20/1) to obtain 1.00 g of the title compound as crystals. This compound is No. 6 in Table 1. m.p.: 116.0°-117.0° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (Solvent: Chloroform/Methanol=20/1)

Sources & evidence

ORD record
ord-413423d140104099ae13a250c643f00b
Source dataset
uspto-grants-1992_11
Patent number
US05166164

Reaction notes

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