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

HRID 253192Notes

Reaction equation

HRID 253192 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]>>[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

4

Reactant 3

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

Product 1

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

Procedure

To a mixture of 2,4-dinitrobenzaldehyde (6.45 g, 32.9 mol) and K2CO3 (5.45 g, 39.4 mmol) in DMIF (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-22503dec7c314c7984c6191673ac213a
Source dataset
uspto-grants-2011_01
Patent number
US07872024B2

Reaction notes

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