Acetic Acid → 1-(6-Chloro-3-pyridylmethyl)-1,3,3-trimethyl-2-nitroguanidine

HRID 1781595Notes

Reaction equation

HRID 1781595 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([N:15]([CH3:17])[CH3:16])=[N:11][N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1.[H-].[Na+].IC.[C:22](O)(=O)C>O1CCCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([CH3:22])[C:10]([N:15]([CH3:17])[CH3:16])=[N:11][N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1362181971-(6-Chloro-3-pyridylmethyl)3,3-dimethyl-2-nitroguanidine

Product 1

HCID 539730491-(6-Chloro-3-pyridylmethyl)-1,3,3-trimethyl-2-nitroguanidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 0.24 g of 1-(6-chloro-3-pyridylmethyl)-3,3-dimethyl-2-nitroguanidine (Compound No. 6) and 6 ml of dry tetrahydrofuran (THF) was added 0.045 g of 60% sodium hydride (in mineral oil) at room temperature, followed by stirring for 30 minutes. A solution of 0.16 g of iodomethane in 1 ml of THF was added to the reaction mixture and allowed to react for 3 days. After adding 0.1 ml of acetic acid, the mixture was filtered to remove insoluble materials and the filtrate was concentrated. The residue was purified by a column chromatography [developing solvent: dichloromethanemethanol (20:1)] to obtain 0.17 g of 1-(6-chloro-3-pyridylmethyl)-1,3,3-trimethyl-2-nitroguanidine (Compound No. 14) as a white solid.

Workup

  1. customto react for 3 days
  2. filtrationthe mixture was filtered
  3. customto remove insoluble materials
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by a column chromatography [developing solvent: dichloromethanemethanol (20:1)]

Sources & evidence

ORD record
ord-bdd54f199ffc42b194e4d4d34c788ac0
Source dataset
uspto-grants-1997_05
Patent number
US05633375

Reaction notes

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