Dimethylformamide → 2,1,3-Benzoxadiazole-5-carbonitrile

HRID 1776339Notes

Reaction equation

HRID 1776339 reaction equation
[CH2:1]1[CH:5]2[CH:6]([C:8]3ON=C(N)[N:9]=3)C[N:3]([CH2:4]2)[CH2:2]1.[C:14]([Cu])#[N:15].CN(C=[O:21])C>O>[N:15]1[O:21][N:9]=[C:8]2[CH:6]=[C:5]([C:4]#[N:3])[CH:1]=[CH:2][C:14]=12

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 1639383-(3-Amino-1,2,4-oxadiazol-5-yl)-1-azabicyclo(2.2.1)heptaneHCID 178418546HCID 178418546, compound

Product 1

HCID 27354522,1,3-Benzoxadiazole-5-carbonitrileYield 48%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

To a stirred solution of 5-bromobenzo[c][1,2, and 5]oxadiazole (2.0 G, 10.050 mmol) in DMF (50 mL) was added CuCN (1.79 g, 230.10 mmol) at RT under an inert atmosphere. The reaction mixture was then heated at 140° C. for 24 h., cooled to RT, diluted with water (10 mL) and stirred for 10 min. The precipitated solid was filtered off and the filtrate was concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford benzo[c][1,2,5]oxadiazole-5-carbonitrile (0.7 g, 48%) as a yellow solid.

Workup

  1. temperaturecooled to RT
  2. filtrationThe precipitated solid was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customto obtain the crude product
  5. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-dc6f49ff3c8d44b4a167a847bbe673b9
Source dataset
uspto-grants-2016_02
Patent number
US09265767B2

Reaction notes

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