Sodium hydride → 4-Methoxy-2-(3-methyl-1,2,4-oxadiazol-5-yl)benzenamine

HRID 53244

Reaction equation

HRID 53244 reaction equation
[H-].[Na+].[C:3](=[N:6][OH:7])([NH2:5])[CH3:4].[NH2:8][C:9]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:10]=1[C:11](OC)=O>O1CCCC1>[CH3:20][O:19][C:16]1[CH:17]=[CH:18][C:9]([NH2:8])=[C:10]([C:11]2[O:7][N:6]=[C:3]([CH3:4])[N:5]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 30926N-HydroxyacetamidineHCID 13052275Methyl 2-amino-5-methoxybenzoate

Product 1

HCID 199621234-Methoxy-2-(3-methyl-1,2,4-oxadiazol-5-yl)benzenamineYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (594 mg) was added to a stirred suspension of acetamide oxime (1.0 g) and 4 molecular sieves (4 g) in dry tetrahydrofuran (50 ml) under nitrogen. The mixture was heated at 60° for 30 min then allowed to cool to room temperature. A solution of 2-amino-5-methoxybenzoic acid, methyl ester (2.0 g) in dry tetrahydrofuran (20 ml) was added and the mixture stirred at reflux for 2.5 h. The suspension was allowed to cool, filtered and the filtrate evaporated to give the title compound as a yellow solid (1.64 g)

Workup

  1. temperatureThe mixture was heated at 60° for 30 min
  2. temperatureat reflux for 2.5 h
  3. temperatureto cool
  4. filtrationfiltered
  5. customthe filtrate evaporated

Sources & evidence

ORD record
ord-de14df84f908491bba4e59f0038f2dee
Source dataset
uspto-grants-1997_04
Patent number
US05618827

Linked notes

Loading…