Triethylamine → 1-(2-Chloro-5-pyridylmethyl)-5-methyl-2-nitroiminohexahydro-1,3,5-triazine

HRID 635171Notes

Reaction equation

HRID 635171 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]([NH:12][N+:13]([O-:15])=[O:14])=[NH:11])=[CH:4][N:3]=1.Cl[CH2:17][N:18]([CH2:20]Cl)[CH3:19].C(N(CC)CC)C>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:19][N:18]([CH3:20])[CH2:17][NH:11][C:10]2=[N:12][N+:13]([O-:15])=[O:14])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15564962BischloromethylmethylamineHCID 178512104HCID 178512104, compound

Product 1

HCID 1364010691-(2-Chloro-5-pyridylmethyl)-5-methyl-2-nitroiminohexahydro-1,3,5-triazineYield 104.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

0.6 g of 1-(2-chloro-5-pyridylmethyl)-3-nitroguanidine and 0.4 g of bis(chloromethyl)methylamine were suspended in dried THF. To the suspension, a solution of 0.52 g of triethylamine in THF was added dropwise with cooling. The reaction mixture was stirred for 1 hour, and then poured into ice water. The mixture was extracted with dichloromethane. After the extract was dried over anhydrous magnesium sulfate, dichloromethane was distilled off. The residue was recrystallized from methanol to obtain 0.78 g of the title compound. This compound is No. 1 in Table 1. m.p.: 150-154° C.

Workup

  1. temperaturewith cooling
  2. extractionThe mixture was extracted with dichloromethane
  3. dry with materialAfter the extract was dried over anhydrous magnesium sulfate, dichloromethane
  4. distillationwas distilled off
  5. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-b8a231d5e9bd4d2b9eef8efd7e80be4e
Source dataset
uspto-grants-2001_02
Patent number
US06187773B1

Reaction notes

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