Sodium Iodide → HCID 22100480, compound

HRID 1457759Notes

Reaction equation

[I-].[Na+].Cl[Si](C)(C)C.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([O:33][CH3:34])=[C:13]([CH:32]=1)[C:14]([NH:16][CH:17]1[CH:26](O)[C:25]2[C:20](=[CH:21][C:22]([O:28][CH3:29])=[CH:23][CH:24]=2)[O:19][C:18]1([CH3:31])[CH3:30])=[O:15].S(=O)(O)[O-].[Na+]>C(#N)C>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([O:33][CH3:34])=[C:13]([CH:32]=1)[C:14]([NH:16][CH:17]1[CH2:26][C:25]2[C:20](=[CH:21][C:22]([O:28][CH3:29])=[CH:23][CH:24]=2)[O:19][C:18]1([CH3:30])[CH3:31])=[O:15]

Participants

Conditions

Temperature: 25 °C

Procedure

44 g (300 mmol) of sodium iodide and 38 ml (300 mmol) of chlorotrimethylsilane were added to 19.6 g (50 mmol) of 3-(5-chloro-2-methoxybenzamido)-2,2-dimethyl-7-methoxy-4-chromanol in 120 ml of acetonitrile. The temperature rose temporarily to 32° C. After the mixture had been stirred at about 25° C. for three hours, it was poured into ice/water, decolorized with concentrated sodium bisulfite solution and extracted several times with methylene chloride. The combined organic solutions were washed with water, dried and evaporated and the residue was chromatographed over a silica gel column using methylene chloride/ethyl acetate 95:5. The 3-(5-chloro-2-methoxybenzamido)-2,2-dimethyl-7-methoxychroman was obtained as an oil.

Workup

customrose temporarily to 32° C
extractionextracted several times with methylene chloride
washThe combined organic solutions were washed with water
customdried
customevaporated
customthe residue was chromatographed over a silica gel column

Sources & evidence

ORD record: ord-a1317c5ff11f4d9884267d3f487c2d9f
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849755

Reaction notes

Loading…