Water → HCID 118098694, compound
Reaction equation
Cl[C:2]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:3]=1[CH2:4][N:5]([CH3:16])[C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[S-2:24].[Na+].[Na+].O>CS(C)=O>[SH:24][C:2]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:3]=1[CH2:4][N:5]([CH3:16])[C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
To a partially dissolved mixture of 6A (7.00 g, 20.91 mmol) in DMSO (40 mL), was added sodium sulfide (3.26 g, 41.8 mmol). The mixture was stirred at 50° C. for 45 min. The reaction mixture was cooled to rt, poured into water (500 mL). The mixture was extracted with EtOAc (3×). The combined organic phase was washed with water and brine, filtered though a pad of SiO2 and concentrated to a red oil. The crude product was purified by flash chromatography (loaded in chloroform onto a 40 g column and eluted with a gradient from 0 to 100% ethyl acetate/hexanes). The desired fractions were collected, concentrated to give 6B (3.10 g, 9.33 mmol, 44.6% yield) as an orange solid. 1H NMR (400 MHz, chloroform-d) δ ppm 7.99 (d, J=7.15 Hz, 2H) 7.27-7.48 (m, 6H) 5.20 (br. s., 2H) 4.56 (br. s., 2H) 2.96 (br. s., 3H); MS (ESI) m/z: 333.1 [M+1]+.
Workup
- temperatureThe reaction mixture was cooled to rt
- extractionThe mixture was extracted with EtOAc (3×)
- washThe combined organic phase was washed with water and brine
- filtrationfiltered though a pad of SiO2
- concentrationconcentrated to a red oil
- customThe crude product was purified by flash chromatography (
- washeluted with a gradient from 0 to 100% ethyl acetate/hexanes)
- customThe desired fractions were collected
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-a746611272964b20b7d9e05fcadbc6d8
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09174974B2
Reaction notes
Loading…