Cyanamide → Benzotriazole-1-carboxamidinium tosylate

HRID 1827807Notes

Reaction equation

HRID 1827807 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1.[N:10]#[C:11][NH2:12].O.[C:14]1([CH3:24])[CH:19]=[CH:18][C:17]([S:20]([OH:23])(=[O:22])=[O:21])=[CH:16][CH:15]=1>O1CCOCC1.CCOCC>[C:14]1([CH3:24])[CH:15]=[CH:16][C:17]([S:20]([OH:23])(=[O:21])=[O:22])=[CH:18][CH:19]=1.[C:11]([N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[N:2]1)(=[NH:10])[NH2:12]

Participants

6

Reactant 3

HCID 9864CyanamideHCID 521998p-Toluenesulfonic acid monohydrateHCID 178418385HCID 178418385, compound

Product 1

HCID 11221277Benzotriazole-1-carboxamidinium tosylate

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of benztriazole (11.9 g, 100 mmol), cyanamide (4.2 g, 100 mmol), and p-toluene sulfonic acid hydrate (19.2 g, 100 mmol) in dioxane was refluxed for 24 hours. The reaction mixture was allowed to cool to room temperature and was diluted with ether, stirred vigorously, then filtered. The filter cake was washed with ether and recrystallized from ethanol to give the desired product as a white solid.

Workup

  1. temperaturewas refluxed for 24 hours
  2. filtrationfiltered
  3. washThe filter cake was washed with ether
  4. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-9a7235626b7d479780b0700bb5cfdf04
Source dataset
uspto-grants-2006_06
Patent number
US07056915B2

Reaction notes

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