Hydrochloric Acid → 3-iodo-5-(2H-tetrazol-5-yl)pyridin-2-amine

HRID 2199616Notes

Reaction equation

[I:1][C:2]1[C:3]([NH2:10])=[N:4][CH:5]=[C:6]([N+]#[C-])[CH:7]=1.[Cl-].[NH4+].[N-:13]=[N+:14]=[N-:15].[Na+].Cl.[CH3:18][N:19](C)C=O>CO.C(Cl)(Cl)Cl.O>[I:1][C:2]1[C:3]([NH2:10])=[N:4][CH:5]=[C:6]([C:18]2[N:13]=[N:14][NH:15][N:19]=2)[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To the solution of 3-iodo-5-isocyanopyridin-2-amine (2.74 g, 11.2 mmol, 1 eq) in anhydrous dimethylformamide (25 mL) in a 100 mL round bottom flask was added ammonium chloride (1.02 g, 1.7 eq) and sodium azide (1.24 g, 1.7 eq). The resulting reaction mixture was heated to 100° C. under nitrogen for 20 hours. After the reaction mixture was cooled to room temperature, it was poured into ice-chunk filled water and the pH of the mixture was adjusted to ˜3.5 using aqueous hydrochloric acid (2 N). After the mixture was stirred at room temperature for about two hours, it was filtered through a Buchner funnel, rinsed with water, giving a brown solid. The solid was treated with MeOH—CHCl3 and concentrated down with silica gel. Upon gradient column chromatography (MeOH-EtOAc 1:20 to 1:5), 3-iodo-5-(2H-tetrazol-5-yl)pyridin-2-amine was obtained as off-white solid in the amount of 1.15 g.

Workup

customThe resulting reaction mixture
temperatureAfter the reaction mixture was cooled to room temperature
additionit was poured into ice-chunk
filtrationit was filtered through a Buchner funnel
washrinsed with water
customgiving a brown solid
concentrationconcentrated down with silica gel

Sources & evidence

ORD record: ord-d4989998e5e64a669ce91e960fe52142
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09359336B2

Reaction notes

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