Triethylamine → 2-(1H-Benzoimidazol-2-YL)-2H-[1,2,4]triazol-3-ylamine

HRID 553020

Reaction equation

HRID 553020 reaction equation
[NH:1]([C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=1)[NH2:2].C(N(CC)CC)C.C(O[CH:22]=[N:23][C:24]#[N:25])C>C(O)C>[NH2:25][C:24]1[N:1]([C:3]2[NH:4][C:5]3[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=3[N:7]=2)[N:2]=[CH:22][N:23]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 957882-hydrazinyl-1H-1,3-benzodiazoleHCID 9920370Methanimidic acid, N-cyano-, ethyl ester

Product 1

HCID 6082642-(1H-Benzoimidazol-2-YL)-2H-[1,2,4]triazol-3-ylamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-hydrazino-1H-benzimidazole (5.0 g, 33.7 mmol) in ethanol (30 ml) is added sequentially triethylamine (5 ml, 33.7 mmol) and N-cyanoformimidic acid ethyl ester (3.3 g, 33.7 mmol) with cooling. After stirring for 2 hours at 0° C. the resulting precipitate is filtered with suction and dried to give 3-amino-2-(1H-benzimidazol-2-yl)-1,2,4-triazole. 1H-NMR (400 MHz, d6-DMSO): 13.0 (s, 1H); 7.77 (s, 1H); 7.70 (m, 2H); 7.50 (m, 2H); 7.20 (s, 2H).

Workup

  1. temperaturewith cooling
  2. filtrationis filtered with suction
  3. customdried

Sources & evidence

ORD record
ord-7f981c4fd9b14cffba505597659955b4
Source dataset
uspto-grants-2011_05
Patent number
US07951957B2

Linked notes

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