4-Ethoxyaniline → HCID 68648008, compound

HRID 1161756Notes

Reaction equation

HRID 1161756 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH2:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])[O:4][N:3]=1.[CH3:17]OC(OC)N(C)C.[CH3:25][CH2:26][O:27][C:28]1[CH:29]=[CH:30][C:31]([NH2:34])=[CH:32][CH:33]=1>C1(C)C=CC=CC=1>[CH2:26]([O:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][CH:17]=[C:7]([C:5]2[O:4][N:3]=[C:2]([CH3:1])[CH:6]=2)[C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:9])=[CH:30][CH:29]=1)[CH3:25]

Participants

5

Reactant 3

HCID 90764-EthoxyanilineHCID 78373Dimethylformamide dimethyl acetalHCID 24763722HCID 24763722, compound

Product 1

HCID 68648008HCID 68648008, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 3-methyl-N-phenyl-5-isoxazoleacetamide (10 mmol) and N,N-dimethyl-formamide dimethyl acetal (1.80 g, 2.0 mL, 15 mmol) in 20 mL of toluene was stirred at 80° C. for 24 h. The reaction was conc. to dryness. The residue was dissolved in 5 mL of toluene and treated with neat p-phenetidine (10 mmol). After heating at reflux for 2 h, the reaction was evaporated to dryness. Purification by column chromatography (2% MeOH/CH2Cl2) afforded the title compound as a light yellow solid, mp 114-115° C.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 2 h
  3. customthe reaction was evaporated to dryness
  4. customPurification by column chromatography (2% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-53b09706b9574897a02e86904ddae34d
Source dataset
uspto-grants-2010_10
Patent number
US07820663B2

Reaction notes

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