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

HRID 545456Notes

Reaction equation

HRID 545456 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 hr. 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 hr
  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-e02af17b932b49028b3dfb2146cfb7b1
Source dataset
uspto-grants-2011_05
Patent number
US07935724B2

Reaction notes

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