Sulfuric Acid → 2-(3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)benzamide

HRID 1974326Notes

Reaction equation

HRID 1974326 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[N:11]=[N:10]1)#[N:2].S(=O)(=O)(O)[OH:19].[OH-].[NH4+]>>[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[C:13]2=[N:14][CH:15]=[CH:16][CH:17]=[C:12]2[N:11]=[N:10]1)(=[O:19])[NH2:2]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 124454992-(3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)benzonitrile

Product 1

HCID 124455002-(3H-[1,2,3]Triazolo[4,5-b]pyridin-3-yl)benzamide

Procedure

The cyano compound (from Example 7) (600 mg.) was dissolved in 8 ml. of concentrated sulfuric acid with ice cooling. After standing at room temperature for 7 hours it was poured onto ice. The cold solution was treated with an excess of ammonium hydroxide. The precipitate was collected, air dried and recrystallized from dimethylformamide and water to give 3-(2-carbamoylphenyl)-3H-1,2,3-triazolo[4,5-b]pyridine, m.p. >340° C.

Workup

  1. additionit was poured onto ice
  2. customThe precipitate was collected
  3. customair dried
  4. customrecrystallized from dimethylformamide and water

Sources & evidence

ORD record
ord-9bf51204d5484c06a9628526e635a6d7
Source dataset
uspto-grants-1976_12
Patent number
US04000286

Reaction notes

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