Potassium Carbonate → Methyl 6-nitro-1-benzothiophene-2-carboxylate

HRID 500674Notes

Reaction equation

HRID 500674 reaction equation
[N+]([C:4]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:5]=1[CH:6]=O)([O-])=O.C([O-])([O-])=O.[K+].[K+].[C:21]([O:25][CH3:26])(=[O:24])[CH2:22][SH:23]>CN(C=O)C>[CH3:26][O:25][C:21]([C:22]1[S:23][C:4]2[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:5]=2[CH:6]=1)=[O:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 16907Methyl ThioglycolateHCID 682502,4-Dinitrobenzaldehyde

Product 1

HCID 23626901Methyl 6-nitro-1-benzothiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2,4-dinitrobenzaldehyde (6.45 g, 32.9 mmol) and K2CO3 (5.45 g, 39.4 mmol) in DMF (60 mL) was slowly added methyl thioglycolate (3.0 mL, 32.9 mmol). The mixture was stirred at RT for 1 h, then at 50° C. for 2 h. The resultant mixture was poured into H2O/ice and stirred until a precipitate formed. The solid was filtered and triturated with hot MeOH. The pale brown solid was filtered. 1H NMR (DMSO-d6) δ 9.13 (s, 1H), 8.33 (s, 1H), 8.30-8.17 (m, 2H), 3.89 (s, 3H). MS (EI): cal'd (MH+) 238.01, exp (MH+) 238.10.

Workup

  1. waitat 50° C. for 2 h
  2. stirringstirred until a precipitate
  3. customformed
  4. filtrationThe solid was filtered
  5. customtriturated with hot MeOH
  6. filtrationThe pale brown solid was filtered

Sources & evidence

ORD record
ord-2d5945e76a9944da95754e8e7bef401a
Source dataset
uspto-grants-2010_08
Patent number
US07772238B2

Reaction notes

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