Cyanogen Bromide → 5-[4-(Trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-amine

HRID 1023200Notes

Reaction equation

HRID 1023200 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:12]=[CH:11][C:6]([C:7]([NH:9][NH2:10])=[O:8])=[CH:5][CH:4]=1.C(=O)(O)[O-].[Na+].[N:20]#[C:21]Br>O1CCOCC1.O>[F:1][C:2]([F:13])([F:14])[C:3]1[CH:12]=[CH:11][C:6]([C:7]2[O:8][C:21]([NH2:20])=[N:10][N:9]=2)=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 5206624-(Trifluoromethyl)benzohydrazide

Product 1

HCID 52160855-[4-(Trifluoromethyl)phenyl]-1,3,4-oxadiazol-2-amineYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(trifluoromethyl)benzohydrazide (0.5 g, 2.449 mmol) in dioxane (10 mL) and water (2 mL) was added sodium bicarbonate (0.617 g, 7.35 mmol) and cyanic bromide (0.519 g, 4.90 mmol). The reaction was stirred at room temperature for 15 h. The reaction mixture was diluted with water (50 mL), extracted with EtOAc, dried over sodium sulfate, and evaporated to yield 5-(4-(trifluoromethyl)phenyl)-1,3,4-oxadiazol-2-amine (0.28, 50%). 1H NMR: 400 MHz, DMSO-d6: δ 7.43 (s, 2H), 7.91 (d, J=8.40 Hz, 2H), 8.00 (d, J=8.40 Hz, 2H). LCMS: RT 1.55 min. LCMS (ES-API), m/z 230.0 (M+H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-458df4e5b20243b1b4238d47b11dfe5c
Source dataset
uspto-grants-2014_05
Patent number
US08722670B2

Reaction notes

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