Water → Ethyl 5-nitro-1-benzothiophene-2-carboxylate

HRID 500676Notes

Reaction equation

HRID 500676 reaction equation
Cl[C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[CH:4]=O.C([O-])([O-])=O.[K+].[K+].[CH2:19]([O:21][C:22](=[O:25])[CH2:23][SH:24])[CH3:20].O>CN(C=O)C>[CH2:19]([O:21][C:22]([C:23]1[S:24][C:2]2[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=2[CH:4]=1)=[O:25])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 12185Ethyl ThioglycolateHCID 729332-Chloro-5-nitrobenzaldehyde

Product 1

HCID 737499Ethyl 5-nitro-1-benzothiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-chloro-5-nitro-benzaldehyde (31.01 g, 167.1 mmol) in 330 mL of anhydrous DMF at 0° C. was added K2CO3 (27.80 g, 201.1 mmol), followed by slow addition of mercapto-acetic acid ethyl ester (18.5 mL, 168.7 mmol). After stirring at 0° C. for 20 min, the resulting mixture was allowed to warm to rt and stir at rt overnight. The reaction mixture was then poured into 1.5 L of water. The solid formed was filtered and washed with 600 μL of water. After drying, 5-nitro-benzo[b]thiophene-2-carboxylic acid ethyl ester was obtained as pale solid. MS (EI): cal'd 252.0 (MH+), exp 252.1 (MH+).

Workup

  1. temperatureto warm to rt
  2. stirringstir at rt overnight
  3. customThe solid formed
  4. filtrationwas filtered
  5. washwashed with 600 μL of water
  6. customAfter drying

Sources & evidence

ORD record
ord-542c1b559c654e10aa5dbdf6eed65203
Source dataset
uspto-grants-2010_08
Patent number
US07772238B2

Reaction notes

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