Cyanogen Bromide → 5-(2,4-Dimethylphenyl)-1,3,4-oxadiazol-2-amine

HRID 868750Notes

Reaction equation

HRID 868750 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]([NH:6][NH2:7])=[O:5].[N:13]#[C:14]Br.C([O-])(O)=O.[Na+]>O1CCOCC1.O>[CH3:1][C:2]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:3]=1[C:4]1[O:5][C:14]([NH2:13])=[N:7][N:6]=1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 48461732,4-Dimethylbenzohydrazide

Product 1

HCID 201200795-(2,4-Dimethylphenyl)-1,3,4-oxadiazol-2-amineYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2,4-dimethylbenzohydrazide (example 16b) (2 g) in dry dioxane (12 mL) was added cyanic bromide (1.28 g, 12.2 mmol) followed by a solution of NaHCO3 (1.02 g, 12.2 mmol) in water (12 mL). The resulting mixture was stirred 2 hours at rt. The solution was concentrated to ½ volume on vacuum and diluted with water (20 mL). The resulting solid was collected and dried on vacuum to give 5-(2,4-Dimethylphenyl)-1,3,4-oxadiazol-2-amine (1.88 g, 82%) as a white solid. 1H NMR (300 MHz, dMSO): δ 2.29 (s, 3H), 2.52 (d, 3H), 7.13 (d, 1H), 7.16 (s, 3H), 7.54-7.56 (d, 1H); MS (M+H, 190).

Workup

  1. concentrationThe solution was concentrated
  2. additiondiluted with water (20 mL)
  3. customThe resulting solid was collected
  4. customdried on vacuum

Sources & evidence

ORD record
ord-1fc9b3efca8044fdb9cd75ba51fd82b8
Source dataset
uspto-grants-2015_03
Patent number
US08968708B2

Reaction notes

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