Dimethyl Sulfoxide → HCID 18516326, compound
Reaction equation
[C:1](Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([OH:32])[C:19]2[CH:24]=[N:23][CH:22]=[C:21]3[S:25][C:26]([C:28]([O:30][CH3:31])=[O:29])=[CH:27][C:20]=23)=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl.CS(C)=O.ClCCl>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:19]2[C:20]3[C:21]([S:25][CH:26]([C:28]([O:30][CH3:31])=[O:29])[CH:27]=3)=[CH:22][N:23]([CH3:1])[CH:24]=2)=[O:32])=[CH:14][CH:13]=1Participants
Conditions
- Temperature
- 78 °C
Procedure
To a stirred solution of oxalyl chloride (0.023 mL, 0.26 mmol) in anhydrous dichloromethane (1 mL) at −78° C. was added DMSO (0.045′mL, 0.63 mmol). After 15 minutes, a solution of Example 237G (0.07 g, 0.21 mmol) in anhydrous 1:4 DMSO/dichloromethane (5 mL) was added dropwise. The reaction was stirred 1 hour at 78° C. then treated with triethylamine (0.15 mL, 1.05 mmol). After 5 minutes, reaction was allowed to warm to room temperature over 1 hour. The reaction was quenched with water (2 mL) and partitioned between EtOAc (50 mL) and sat. aq. NaHCO3 (50 mL). The organic layer was washed with 50% sat. aq. NaHCO3 (2×50 mL), brine (1×50 mL), dried (Na2SO4), filtered, and concentrated. The product was dried in a desiccator to yield the title compound as a white solid (0.07 g, 100%).
Workup
- waitAfter 5 minutes
- customreaction
- temperatureto warm to room temperature over 1 hour
- customThe reaction was quenched with water (2 mL)
- custompartitioned between EtOAc (50 mL) and sat. aq. NaHCO3 (50 mL)
- washThe organic layer was washed with 50% sat. aq. NaHCO3 (2×50 mL), brine (1×50 mL)
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated
- customThe product was dried in a desiccator
Sources & evidence
- ORD record
- ord-623388393533449889528438843dda79
- Source dataset
- uspto-grants-2001_05
- Patent number
- US06232320B1
Reaction notes
Loading…