Cyanamide → Benzotriazole-1-carboxamidinium tosylate

HRID 915207Notes

Reaction equation

HRID 915207 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-0d32334ef9dc467a9ec36bb78740dd89
Source dataset
uspto-grants-2007_09
Patent number
US07265132B2

Reaction notes

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