6-Chloro-N-methyl-3-pyridinemethanamine → 1-[(6-Chloro-3-pyridinyl)methyl]-1-methyl-3-nitroguanidine

HRID 373793Notes

Reaction equation

HRID 373793 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][CH3:10])=[CH:4][CH:3]=1.CS[C:13](=[NH:18])[NH:14][N+:15]([O-:17])=[O:16]>C(O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH3:10])[C:13]([NH:14][N+:15]([O-:17])=[O:16])=[NH:18])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 110948836-Chloro-N-methyl-3-pyridinemethanamineHCID 135927615N-Nitro-S-methylisothiourea

Product 1

HCID 1359912341-[(6-Chloro-3-pyridinyl)methyl]-1-methyl-3-nitroguanidineYield 75.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 13.8 g of 6-chloro-N-methyl-3-pyridinemethanamine, 10.8 g of S-methyl-N-nitroisothiourea and 60 ml of ethanol was heated at 50° C. with stirring for 2 hours and then refluxed for additional 5 hours. After cooling, the separated crystal was collected by filtration, washed with a small amount of ethanol, and dried to obtain 14.7 g of the title compound. This compound is No.1 in Table 1. m.p.: 158.0° C. (Decomposed).

Workup

  1. temperaturerefluxed for additional 5 hours
  2. temperatureAfter cooling
  3. filtrationthe separated crystal was collected by filtration
  4. washwashed with a small amount of ethanol
  5. customdried

Sources & evidence

ORD record
ord-431e28fdc8564e0d8b50aaa4cda1bd0a
Source dataset
uspto-grants-1992_11
Patent number
US05166164

Reaction notes

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