Ethyl Thioglycolate → HCID 10561741, compound

HRID 591033Notes

Reaction equation

HRID 591033 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6](=[O:9])[CH2:7][SH:8])[CH3:4].Cl[C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[C:12]=1[C:13]#[N:14]>CN(C)C=O>[NH2:14][C:13]1[C:12]2[C:15]([CH3:19])=[CH:16][CH:17]=[CH:18][C:11]=2[S:8][C:7]=1[C:6]([O:5][CH2:3][CH3:4])=[O:9]

Participants

5

Reactant 3

HCID 12185Ethyl ThioglycolateHCID 230532-Chloro-6-methylbenzonitrileHCID 24758Sodium hydride

Product 1

HCID 10561741HCID 10561741, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

At 0° C., sodium hydride, 60% dispersion in mineral oil, (280 mg, 7 mmol) was added to a solution of ethyl-2-mercaptoacetate (750 μL, 6.8 mmol) in N,N-dimethylformamide (20 mL). After 15 minutes, 2-chloro-6-methylbenzonitrile (1 g, 6.60 mmol) was also added to the mixture which was stirred at room temperature for 2 hours more. The mixture was then concentrated and the residue was diluted with ethyl acetate. The organic layer was washed with water (30 mL), brine (30 mL), dried over sodium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (cyclohexane/dichloromethane 50/50) to afford the desired benzothiophene (23a) as a white solid (800 mg, 3.40 mmol, 52%).

Workup

  1. concentrationThe mixture was then concentrated
  2. additionthe residue was diluted with ethyl acetate
  3. washThe organic layer was washed with water (30 mL), brine (30 mL)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was purified by flash chromatography on silica gel (cyclohexane/dichloromethane 50/50)

Sources & evidence

ORD record
ord-5542ef4733384dd09a769f9aed83941b
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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