Sodium Carbonate → HCID 10901505, compound

HRID 1936563Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:16][CH3:17])=[C:6]([C:8](=[O:15])[CH2:9][N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)[CH:7]=1.ClC1C=CC=C(C(OO)=[O:26])C=1.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl.O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:16]([CH3:17])=[O:26])=[C:6]([C:8](=[O:15])[CH2:9][N:10]2[CH:14]=[CH:13][CH:12]=[CH:11]2)[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred cooled solution of 1-[5-Fluoro-2-(methylthio)phenyl]-2-(pyrrol-1-yl)ethanone (22c) (1.76 g, 7.06 mmol) in dichloromethane (12 ml) was added dropwise in 30 minutes a solution of m-chloroperbenzoic acid (71.5% grade, 1.70 g, 7.06 mmol) in dichloromethane (10 ml). After stirring for 45 minutes at 0° C., the mixture was treated with a 5% solution of sodium carbonate in water (41 ml) and was stirred for 15 minutes at room temperature. The organic phase was separated and water was extracted with dichloromethane (3×10 ml). The organic layers were dried and evaporated, the residue was chromatographed (10% dichloromethane in ethyl acetate) to afford 1.02 g of 23c as white crystals that darkened rapidly (64% yield). 1H NMR (CDCl3) δ8.42-8.35 (m, 1H); 7.61-7.51 (m, 2H); 6.68-6.62 (m, 2H); 6.26-6.24 (m, 2H); 5.41-5.17 (q, 2H, J=31.32, 17.87 Hz); 2.77 (s, 3H).

Workup

stirringwas stirred for 15 minutes at room temperature
customThe organic phase was separated
extractionwater was extracted with dichloromethane (3×10 ml)
customThe organic layers were dried
customevaporated
customthe residue was chromatographed (10% dichloromethane in ethyl acetate)

Sources & evidence

ORD record: ord-2f48c3e14a644d8cabecc3f4c8e6c08b
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06391870B2

Reaction notes

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