反応 #60785

反応方程式

Methylamine

glycolaldehyde dimer

1-{[isocyano(phenyl)methyl]sulfonyl}-4-methylbenzene

→

(1-Methyl-4-phenyl-1H-imidazol-5-yl)methanol

溶媒

THF

反応条件

後処理

1. 1
   温度cooling
2. 2
   その他the reaction temperature below 30° C
3. 3
   その他the solvent evaporated to a volume of 100 mL
4. 4
   workup.ADDITIONWater (500 mL) was added
5. 5
   ろ過the title compound (4.94 g, 66%) collected by filtration as a white solid
6. 6
   抽出The filtrate was extracted into EtOAc
7. 7
   その他dried
8. 8
   その他the solvent removed in vacuo
9. 9
   その他The residue was triturated with EtOAc
10. 10
    その他to give a further 1.06 g (14%) as a white solid

実験手順

Methylamine (33% in industrial methylated spirits, 60.3 mL) was added to a solution of glycolaldehyde dimer (2.7 g) in THF (320 mL). After 75 minutes 1-{[isocyano(phenyl)methyl]sulfonyl}-4-methylbenzene (PhTosMIC) (Org. Syn., 77, 198-205) (10.8 g) was added, cooling to keep the reaction temperature below 30° C. The reaction was stirred for 90 minutes and the solvent evaporated to a volume of 100 mL. Water (500 mL) was added, and the title compound (4.94 g, 66%) collected by filtration as a white solid. The filtrate was extracted into EtOAc, dried, and the solvent removed in vacuo. The residue was triturated with EtOAc to give a further 1.06 g (14%) as a white solid.

出典