Ethyl Thioglycolate → HCID 70818364, compound

HRID 591015Notes

Reaction equation

HRID 591015 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][CH:6]=[CH:5][C:4]=2[C:3]=1[C:12]#[N:13].[SH:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[O-]CC.[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[C:12]([C:3]1[C:2]([S:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[N:8]2)#[N:13]

Participants

6

Reactant 4

HCID 12185Ethyl ThioglycolateHCID 516892Sodium BicarbonateHCID 2723922Sodium ethoxideHCID 70817991HCID 70817991, compound

Product 1

HCID 70818364HCID 70818364, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 6-bromoquinoline-5-carbonitrile (16b) (300 mg, 1.29 mmol), ethyl mercaptoacetate (212 μL, 1.93 mmol) and sodium ethoxide (122.6 mg, 1.80 mmol) in dimethylformamide (10 mL) was stirred at room temperature for 15 hours. A saturated aqueous solution of sodium bicarbonate was added to the mixture. It was extracted twice with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The intermediate ethyl 2-[(5-cyanoquinolin-6-yl)sulfanyl]acetate obtained was reacted with sodium ethoxide (122.6 mg, 1.80 mmol) in dimethylformamide (8 mL) by stirring at 90° C. for 3 hours. The reaction was cooled to room temperature and water was added (10 mL). The resulting precipitate was filtered and washed with water twice and dried under vacuum with phosphorus pentoxide to afford the desired product (16c) as a solid (299 mg, 1.10 mmol, 85%).

Workup

  1. extractionIt was extracted twice with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f6009ef6da345218317a7bc8320b182
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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