Sodium Hydroxide → Dimethyl-(4-nitro-2-oxazol-2-yl-phenyl)-amine

HRID 450100Notes

Reaction equation

HRID 450100 reaction equation
CO[CH:3]([O:20]C)[CH2:4][NH:5][C:6](=O)[C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[N:16]([CH3:18])[CH3:17].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.[OH-].[Na+]>CS(O)(=O)=O>[CH3:18][N:16]([CH3:17])[C:8]1[CH:9]=[CH:10][C:11]([N+:13]([O-:15])=[O:14])=[CH:12][C:7]=1[C:6]1[O:20][CH:3]=[CH:4][N:5]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 14812Phosphorus oxide (P4O10)HCID 68829856N-(2,2-dimethoxyethyl)-2-(dimethylamino)-5-nitrobenzamide

Product 1

HCID 68827592Dimethyl-(4-nitro-2-oxazol-2-yl-phenyl)-amineYield 60%

Reagents, catalysts & solvents 1

HCID 6395Methanesulfonic AcidSolvent2×

Procedure

A solution of N-(2,2-dimethoxyethyl)-2-dimethylamino-5-nitro benzamide (1.1 g, 3.7 mmol) in methane sulphonic acid (5 ml) was added to a slurry of phosphorus pentoxide (2.6 g, 18.51 mmol) in methane sulphonic acid (15 ml) and refluxed overnight. The reaction mixture was cooled to room temperature, poured onto ice water, and then basified with dilute sodium hydroxide and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to a residue. Purification by chromatography over silica gel using 5-30% ethyl acetate/pet ether gave dimethyl-(4-nitro-2-oxazol-2-yl-phenyl)-amine (150 mg, 60%) as solid.

Workup

  1. temperaturerefluxed overnight
  2. additionpoured onto ice water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. customdried
  6. concentrationconcentrated to a residue
  7. customPurification by chromatography over silica gel using 5-30% ethyl acetate/pet ether

Sources & evidence

ORD record
ord-9a75fd167f514b50b8c2b84d344ca2e6
Source dataset
uspto-grants-2013_07
Patent number
US08486962B2

Reaction notes

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