Reaktion #3222

Reaktionsgleichung

water

sodium hydride

2-(tert-butoxycarbonylamino)-4,6-dichloro-5-methoxybenzoic acid

iodomethane

→

title compound

Ausbeute 96.0%

Methyl 2-(tert-butoxycarbonylamino)-4,6-dichloro-5-methoxybenzoate

Ausbeute 96.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigea precipitate formed which
2. 2
   workup.DISSOLUTIONslowly redissolved
3. 3
   workup.STIRRINGTo the resulting stirred solution
4. 4
   workup.STIRRINGAfter stirring at room temperature for 1.5 hr
5. 5
   Extraktionthe resulting mixture extracted with ether
6. 6
   WaschenThe combined ether extracts were washed with brine
7. 7
   Trocknendried (MgSO4)
8. 8
   Filtrationfiltered
9. 9
   Einengenconcentrated

Vorschrift

To a cold (ice bath) stirred solution of 2-(tert-butoxycarbonylamino)-4,6-dichloro-5-methoxybenzoic acid (2.0 g, 5.9 mM) in 20 mL of dry dimethylformamide under a nitrogen atmosphere was added sodium hydride (0.24 g, 5.9 mM); a precipitate formed which slowly redissolved on stirring. To the resulting stirred solution was added iodomethane (8.4 g, 59 mM). After stirring at room temperature for 1.5 hr, the reaction mixture was poured into water and the resulting mixture extracted with ether. The combined ether extracts were washed with brine, dried (MgSO4), filtered and concentrated to leave the title compound as a yellow oil (2.0 g, 96%); MS(CI): 350 (M+H).

Quelle