Water → 5-Amino-1-benzyl-1H-1,2,3-triazole-4-carboxamide

HRID 400972Notes

Reaction equation

[OH-].[Na+].O.[C:4]([CH2:6][C:7]([NH2:9])=[O:8])#[N:5].[CH2:10]([N:17]=[N+:18]=[N-:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CS(C)=O>[NH2:5][C:4]1[N:17]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:18]=[N:19][C:6]=1[C:7]([NH2:9])=[O:8]

Participants

Conditions

Temperature: 25 °C

Procedure

In a separate reactor, DMSO (17.6 g, 16.0 ml) was charged followed by, 32% aqueous NaOH (7.86 g, 5.82 ml, 62.9 mmol, Eq: 1.0) and water (5.00 g, 5.00 ml). A solution of 2-cyanoacetamide (7.93 g, 94.3 mmol, Eq: 1.50) in DMSO (17.6 g, 16.0 ml) was added dropwise over 15 min at 25° C. The previously prepared benzyl azide solution was added dropwise over 4 h at 25° C. The reaction was stirred overnight at 25° C. and water (120 g, 120 ml) was added dropwise over 30 min at 25° C. (exothermic). The resulting suspension was cooled over 30 min to 0° C., stirred at 0° C. for 30 min and filtered. The filter cake was washed with water (40.0 g, 40.0 ml) and was dried at 50° C./5 mbar to give 12.6 g of the title compound.

Workup

temperatureThe resulting suspension was cooled over 30 min to 0° C.
stirringstirred at 0° C. for 30 min
filtrationfiltered
washThe filter cake was washed with water (40.0 g, 40.0 ml)
customwas dried at 50° C./5 mbar

Sources & evidence

ORD record: ord-555ba651cce042679d213a6fdc899af0
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08741906B2

Reaction notes

Loading…