Cyanamide → 1H-Benzotriazole-1-carboximidamide--hydrogen chloride (1/1)

HRID 1192237Notes

Reaction equation

HRID 1192237 reaction equation
[ClH:1].[NH:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1.[N:11]#[C:12][NH2:13]>CCOCC>[ClH:1].[N:2]1([C:12](=[NH:11])[NH2:13])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[N:3]1

Participants

4

Reactant 2

HCID 9864CyanamideHCID 178477914HCID 178477914, compound

Product 1

HCID 534349021H-Benzotriazole-1-carboximidamide--hydrogen chloride (1/1)Yield 71.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

To a 5 mL CEM microwave reaction vessel, was charged benzotriazole HCl salt (0.5 g, 3.2 mmol) and cyanamide (0.16 g, 3.9 mmol). The vessel was sealed and heated at 80° C. for 1 minute under microwave irradiation (CEM Discovery™). After this time, TLC analysis showed no starting material remaining so the mixture was diluted with ether. The precipitate was collected by filtration and washed with ether and dried under vacuum to afford the titled product as a white solid (0.45 g, 71% yield). 1H NMR (400 MHz, d6-DMSO) δ: 10.14 (4H, s), 8.31 (1H, m), 8.05 (1H, m), 7.90 (1H, m), 7.67 ('H, m). MS m/z: 162.13 [M+H]+.

Workup

  1. customTo a 5 mL CEM microwave reaction vessel
  2. customThe vessel was sealed
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with ether
  5. customdried under vacuum

Sources & evidence

ORD record
ord-b8e131378a704e219eeafe209a30c357
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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