Potassium Carbonate → Ethyl 5-nitro-1-benzothiophene-2-carboxylate

HRID 253194Notes

Reaction equation

HRID 253194 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>[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

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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 DMP 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 mL 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 (I).

Workup

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

Sources & evidence

ORD record
ord-803d7babd36148fea511f51b628c51b6
Source dataset
uspto-grants-2011_01
Patent number
US07872024B2

Reaction notes

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