Methyl Thioglycolate → Methyl 6-cyanobenzo[b]thiophene-2-carboxylate
Reaction equation
Cl[C:2]1[C:9]([C:10]#[N:11])=[CH:8][CH:7]=[CH:6][C:3]=1C=O.[H-].[Na+].[SH:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].[CH3:20]S(Cl)(=O)=O>C(OCC)(=O)C>[C:10]([C:9]1[CH:8]=[CH:7][C:6]2[CH:20]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[S:14][C:3]=2[CH:2]=1)#[N:11]Participants
Conditions
- Temperature
- 80 °C
Procedure
2.5 g (15.1 mmol) of 2-chloro-3-cyanobenzaldehyde are reacted according to the general procedure with 0.90 g (22.7 mmol) of sodium hydride (60% pure) and 1.76 g (16.6 mmol) of methyl mercaptoacetate. The resulting reaction product is initially purified by silica gel column chromatography (mobile phase: dichloromethane/methanol 100:1) and then dissolved in 30 ml of pyridine, and 650 μl (8.4 mmol) of methanesulfonyl chloride are added. The mixture is stirred at 80° C. for 2 h. After cooling, ethyl acetate is added and the mixture is washed twice with 1N hydrochloric acid and once with saturated sodium chloride solution, dried over sodium sulfate, concentrated and dried under high vacuum. This gives 1.63 g (49.9% of theory) of the title compound.
Workup
- customThe resulting reaction product
- customis initially purified by silica gel column chromatography (mobile phase: dichloromethane/methanol 100:1)
- dissolutiondissolved in 30 ml of pyridine
- temperatureAfter cooling
- washthe mixture is washed twice with 1N hydrochloric acid and once with saturated sodium chloride solution
- dry with materialdried over sodium sulfate
- concentrationconcentrated
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-cadb99b348c0446fad0682c7241d51cb
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08884017B2
Reaction notes
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