Реакция #3222

Уравнение реакции

water

sodium hydride

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

iodomethane

→

title compound

Выход 96.0%

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

Выход 96.0%

Растворители

dimethylformamide

Условия реакции

Обработка

1. 1
   Другоеa 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
   Экстракцияthe resulting mixture extracted with ether
6. 6
   ПромывкаThe combined ether extracts were washed with brine
7. 7
   Сушкаdried (MgSO4)
8. 8
   Фильтрацияfiltered
9. 9
   Концентрированиеconcentrated

Методика

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).

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