Hydrochloric Acid → 5-(naphthalen-1-yl)-4H-1,2,4-triazol-3-amine

HRID 906822Notes

Reaction equation

[N+]([O-])(O)=O.[NH2:5][NH:6][C:7]([NH2:9])=[NH:8].C[O-].[Na+].[C:13]1([C:23](OC)=O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.Cl>O.CO>[C:13]1([C:23]2[NH:5][N:6]=[C:7]([NH2:9])[N:8]=2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred mixture of N-aminoguanidine nitrate (2.74 g, 20 mmol) and anhydrous methanol (25 mL) cooled to 0° C. was added sodium methoxide solution (25% in methanol, 4.57 mL, 20 mmol) dropwise. The resulting mixture was stirred at 0° C. for 10 min before methyl 1-naphthoate (0.93 g, 5 mmol) was added. The mixture was then stirred at 0° C. for 10 min, RT for 10 min, 70° C. for 22 hr, and 75° C. for 19 hr. The reaction mixture was cooled and diluted with 10 mL of water. Concentration under vacuum gave a slightly cloudy solution which was acidified to pH=3-4 with 3 N aqueous HCl solution. The solid obtained was filtered, washed with water, and triturated with ethanol to give 0.55 g (52% yield) of 5-(naphthalen-1-yl)-1H-1,2,4-triazol-3-amine as a yellow solid. (M+H)+=211.16.

Workup

additionwas added
wait75° C. for 19 hr
temperatureThe reaction mixture was cooled
concentrationConcentration under vacuum
customgave a slightly cloudy solution which
customThe solid obtained
filtrationwas filtered
washwashed with water
customtriturated with ethanol

Sources & evidence

ORD record: ord-7975460126144a51bf6384946fd12408
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08013004B2

Reaction notes

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