Dimethylformamide → 4-(5-Amino-1,3,4-oxadiazol-2-yl)-3-ethyl-2-methylphenol

HRID 388787Notes

Reaction equation

HRID 388787 reaction equation
[N:1]#[C:2]Br.[CH2:4]([C:6]1[C:15]([CH3:16])=[C:14]([OH:17])[CH:13]=[CH:12][C:7]=1[C:8]([NH:10][NH2:11])=[O:9])[CH3:5].C(=O)([O-])O.[Na+].CN(C=O)C>O>[NH2:1][C:2]1[O:9][C:8]([C:7]2[CH:12]=[CH:13][C:14]([OH:17])=[C:15]([CH3:16])[C:6]=2[CH2:4][CH3:5])=[N:10][N:11]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 58298858HCID 58298858, compound

Product 1

HCID 1358628934-(5-Amino-1,3,4-oxadiazol-2-yl)-3-ethyl-2-methylphenolYield 11.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

196 mg of cyanogen bromide are added dropwise to a solution of 300 mg of 2-ethyl-4-hydroxy-3-methylbenzohydrazide in 50 ml of water, 130 mg of sodium hydrogencarbonate and 4 ml of DMF. A gas forms and a precipitate deposits. The latter is filtered off with suction and purified by column chromatography on silica gel, giving 40 mg of 4-(5-amino-1,3,4-oxadiazol-2-yl)-3-ethyl-2-methylphenol as colourless powder; MS-FAB (M+H+)=220; Rf (polar method): 1.43 min;

Workup

  1. filtrationThe latter is filtered off with suction
  2. custompurified by column chromatography on silica gel

Sources & evidence

ORD record
ord-cca37965340a499c8b8cfb5de7a3c74d
Source dataset
uspto-grants-2013_02
Patent number
US08377975B2

Reaction notes

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