反应详情

N-Methyl 4-methylbenzimidoyl chloride (3.85 g, 23 mmole) was treated with alcohol free chloroform (4.5 ml) and chlorosulfonic acid (0.2 g, 1.7 mmole). Methyl 1-methyl-1H-pyrrole-2-acetate (3.5 g, 23 mmole) was added in one portion, the reaction was fitted with a calcium chloride drying tube and stirred overnight. The reaction was quenched with saturated aqueous sodium bicarbonate. The phases were separated and the organic phase was concentrated under reduced pressure. The residue (6.6 g of a red oil) was dissolved in methanol (50 ml) and treated with sodium acetate (3 g, 36 mmole) and water (10 ml). The reaction was heated at reflux overnight, then cooled in an ice bath. The title compound crystallized and was isolated by filtration, washed with cold methanol, and air dried to yield 2.3 g (37%) of a light tan solid, m.p. 117°-119° C.

1. customthe reaction was fitted with a calcium chloride drying tube
2. customThe reaction was quenched with saturated aqueous sodium bicarbonate
3. customThe phases were separated
4. concentrationthe organic phase was concentrated under reduced pressure
5. dissolutionThe residue (6.6 g of a red oil) was dissolved in methanol (50 ml)
6. temperatureThe reaction was heated
7. temperatureat reflux overnight
8. temperaturecooled in an ice bath
9. customThe title compound crystallized
10. customwas isolated by filtration
11. washwashed with cold methanol, and air
12. customdried