Sodium Chloride → HCID 67979692, compound
Reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH2:2][SH:3].Br[C:9]1[C:10]2[S:32][CH:31]=[C:30]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[C:11]=2[S:12][C:13]=1[C:14](=O)[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].[C:48]([O-])([O-])=O.[K+].[K+].[Cl-].[Na+]>CN(C)C=O>[CH2:6]([O:5][C:1]([C:2]1[S:3][C:9]2[C:10]3[S:32][CH:31]=[C:30]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[C:11]=3[S:12][C:13]=2[C:14]=1[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:48])=[O:4])[CH3:7]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
ethyl thioglycolate (0.85 g, 0.77 mL, 7 mmol) was added to a mixture of 4 (4.5 g, 6.74 mmol), K2CO3 (1.86 g, 13.5 mmol), and N,N-dimethylformamide (DMF) (70 mL) at room temperature. The resulting mixture was stirred for 12 hrs at room temperature and another 12 hrs at 50° C. The mixture was then poured into an aqueous sodium chloride solution (100 mL) and extracted with ethyl acetate (150 mL). The organic layer was separated, washed with saturated aqueous sodium chloride solution (4×150 mL), and dried over MgSO4. The crude product was obtained after evaporating off the solvent and used in the next step without further purification (4.2 g, 91% yield).
Workup
- extractionextracted with ethyl acetate (150 mL)
- customThe organic layer was separated
- washwashed with saturated aqueous sodium chloride solution (4×150 mL)
- dry with materialdried over MgSO4
Sources & evidence
- ORD record
- ord-1f115731aa5c40dab22237564911de82
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09166167B2
Reaction notes
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