反応 #3222

反応方程式

water

sodium hydride

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

iodomethane

→

title compound

収率 96.0%

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

収率 96.0%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   その他a 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
   抽出the resulting mixture extracted with ether
6. 6
   洗浄The combined ether extracts were washed with brine
7. 7
   乾燥dried (MgSO4)
8. 8
   ろ過filtered
9. 9
   濃縮concentrated

実験手順

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).

出典