Methanol → N-(2,5-Dimethylphenyl)acetamide

HRID 475932

Reaction equation

HRID 475932 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][C:3]=1[NH2:4].[C:10](OC(=O)C)(=[O:12])[CH3:11].CO>O1CCCC1>[CH3:9][C:6]1[CH:7]=[CH:8][C:2]([CH3:1])=[C:3]([NH:4][C:10]([CH3:11])=[O:12])[CH:5]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 72592,5-DimethylanilineHCID 7918Acetic Anhydride

Product 1

HCID 16304N-(2,5-Dimethylphenyl)acetamideYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2,5-Dimethylaniline 16 (5.0 gm, 0.041 moles) was dissolved in 30 ml tetrahydrofuran (THF) at room temperature under argon. Acetic anhydride (5.9 ml, 0.062 moles) was added. Within 15 minutes, solids formed and the mixture became a solid white mass after 1 hour. Methanol was added which dissolved the mass. The mixture was evaporated under reduced pressure, dissolved in hot DCM and purified by flash chromatography on silica gel, eluting with a mixture of methanol and DCM. 2,5-Dimethylacetanilide 17 (6.67 gm, 99% yield) was isolated after removing the solvent. NMR (CDCl3) δ 7.53, 1H, br s; 6.89-7.06, 3H, m; 2.30, 3H, s; 2.19, 3H, s; 2.17, 3H, s.

Workup

  1. customsolids formed
  2. customafter 1 hour
  3. dissolutiondissolved the mass
  4. customThe mixture was evaporated under reduced pressure
  5. dissolutiondissolved in hot DCM
  6. custompurified by flash chromatography on silica gel
  7. washeluting with a mixture of methanol and DCM

Sources & evidence

ORD record
ord-7029fc6668fe4910a3e1e246048c1d9f
Source dataset
uspto-grants-2014_01
Patent number
US08637658B2

Linked notes

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