Urea → HCID 178488770, compound

Temperature

160 °C

Solid 2-amino-3-methoxybenzaldehyde (37.2 g, 0.246 mole), urea (158 g, 2.5 mole) and catalytic NH4OAc (1 g) were thoroughly mixed together in a roundbottom flask. The solid mixture was heated in a 160° C. bath. The solids quickly melted and stirring was commenced. After about 15 minutes, solids start to precipitate from the hot solution. After adding NMP (150 mL) to dissolve the solids, the reaction was heated with stirring for an additional 30-45 minutes until complete as judged by LCMS. The hot reaction mixture was poured into vigorously stirred water (400 mL). The reaction flask was washed out with water (3×100 mL) and EtOAc (4×50 mL). After stirring ca. 30 minutes, mixture was filtered to collect the light solid precipitate. The solid filter cake was washed with portions of water and EtOAc to give a white solid. The solid was dried on the frit and in vacuo to give the product in 99% purity and 95% yield (41 g, 233 mmole).

1. customto precipitate from the hot solution
2. additionAfter adding NMP (150 mL)
3. dissolutionto dissolve the solids
4. temperaturethe reaction was heated
5. stirringwith stirring for an additional 30-45 minutes until complete
6. additionThe hot reaction mixture was poured into vigorously stirred water (400 mL)
7. washThe reaction flask was washed out with water (3×100 mL) and EtOAc (4×50 mL)
8. stirringAfter stirring ca. 30 minutes
9. filtrationmixture was filtered
10. customto collect the light solid precipitate
11. filtrationThe solid filter cake
12. washwas washed with portions of water and EtOAc
13. customto give a white solid
14. customThe solid was dried on the frit and in vacuo
15. customto give the product in 99% purity and 95% yield (41 g, 233 mmole)

ORD record

ord-d6bc6cd7b12b4a5ea0d56dc573a84d32

Source dataset

uspto-grants-2011_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07932262B2