Hydrochloric Acid → Ethyl 5-nitro-1-benzothiophene-2-carboxylate

HRID 2245799Notes

Reaction equation

HRID 2245799 reaction equation
[H-].[Na+].[SH:3][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].Cl[C:11]1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:12]=1[CH:13]=O.Cl>CN(C)C=O>[CH2:8]([O:7][C:5]([C:4]1[S:3][C:11]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][C:12]=2[CH:13]=1)=[O:6])[CH3:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 12185Ethyl ThioglycolateHCID 24758Sodium hydrideHCID 729332-Chloro-5-nitrobenzaldehyde

Product 1

HCID 737499Ethyl 5-nitro-1-benzothiophene-2-carboxylateYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (60% in mineral oil, 1.3 g, 33.5 mmol) in dimethylformamide (50 mL) was added dropwise ethyl 2-mercaptoacetate (2.95 mL, 27 mmol) at 0° C. under an atmosphere of argon. After stirring at room temperature for 15 minutes, 2-chloro-5-nitrobenzaldehyde was added. The mixture was then stirred at 100° C. for 6 h, cooled to room temperature and poured into hydrochloric acid (250 mL, 1M). The precipitate was filtered off, washed with water (3×50 mL), dried under reduced pressure and recrystallised from ethyl acetate to give the title compound (5.5 g, 82%) as a solid, mp 163° C.

Workup

  1. stirringThe mixture was then stirred at 100° C. for 6 h
  2. temperaturecooled to room temperature
  3. filtrationThe precipitate was filtered off
  4. washwashed with water (3×50 mL)
  5. customdried under reduced pressure
  6. customrecrystallised from ethyl acetate

Sources & evidence

ORD record
ord-3c91b8ebb4f8431fbfce88151f07c7ad
Source dataset
uspto-grants-2010_03
Patent number
US07683185B2

Reaction notes

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