반응 #563114

반응 방정식

2,5-Dimethylaniline

Acetic anhydride

Methanol

→

2,5-Dimethylacetanilide

수율 99.7%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타solids formed
2. 2
   기타after 1 hour
3. 3
   workup.DISSOLUTIONdissolved the mass
4. 4
   기타The mixture was evaporated under reduced pressure
5. 5
   workup.DISSOLUTIONdissolved in hot DCM
6. 6
   기타purified by flash chromatography on silica gel
7. 7
   세척eluting with a mixture of methanol and DCM

실험 절차

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.

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