Sodium Hydroxide → HCID 22603409, compound

A solution of ethyl N-(3,4-dichlorobenzyl)-3-benzylthioindole-2-carboxylate (0.50 g) in dichloromethane (2 ml) was added to a slurry of wet alumina (1 g) and Oxone® (0.615 g) in dichloromethane (10 ml). The mixture was then heated at reflux for two hours, and allowed to cool. The product was washed away from the alumina using methylene chloride (200 ml). The solution was then dried (MgSO4) and evaporated to afford the crude sulphoxide ester (103 mg). The crude ester was dissolved in THF (2 ml) and methanol (1 ml), and sodium hydroxide (2M, 3 ml) was added. The solution was stirred for five hours, then concentrated in vacuo. The residue was dissolved in water (10 ml) and the product precipitated by dropwise addition of aqueous HCl (2M, 10 ml). The resulting solid was collected by filtration and washed with cold water, then dried in vacuo to afford the product as a pale yellow solid (36 mg, 7%. 2 steps), NMR d (CD3SOCD3) 4.37 (d, 2H), 5.83 (d, 2H), 6.96 (dd, 1H), 7.10 (m, 3H), 7.20 (m, 3H), 7.30 (t, 1H), 7.38 (d, 1H), 7.59 (s, 1H), 7.62 (s, 1H), 8.05 (d, 1H); M/z (−) 456 (M−H+), 412, 365, 323, 321, 320.

1. temperatureThe mixture was then heated
2. temperatureat reflux for two hours
3. temperatureto cool
4. washThe product was washed away from the alumina
5. dry with materialThe solution was then dried (MgSO4)
6. customevaporated
7. customto afford the crude sulphoxide ester (103 mg)
8. concentrationconcentrated in vacuo
9. dissolutionThe residue was dissolved in water (10 ml)
10. customthe product precipitated by dropwise addition of aqueous HCl (2M, 10 ml)
11. filtrationThe resulting solid was collected by filtration
12. washwashed with cold water
13. customdried in vacuo

ORD record

ord-3f9db44f63344b43b6525dca0e37b5f4

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06833387B1