Triethylamine → Methyl 6-nitro-1-benzothiophene-2-carboxylate

HRID 15429Notes

Reaction equation

HRID 15429 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.[SH:15][CH2:16][C:17]([O:19][CH3:20])=[O:18].C(N(CC)CC)C>CS(C)=O>[CH3:20][O:19][C:17]([C:16]1[S:15][C:4]2[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:5]=2[CH:6]=1)=[O:18]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 682502,4-Dinitrobenzaldehyde

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

24.8 g (126.7 mmol) of 2,4-dinitrobenzaldehyde, 13.4 g (126.7 mmol) of methyl mercaptoacetate and 35.3 ml (253.3 mmol) of triethylamine in 74.5 ml of DMSO are heated at 80° C. for 1 h. The reaction solution is poured into 250 ml of ice-water. The resulting precipitate is filtered off with suction, washed with water and dried at 50° C. under reduced pressure overnight. This gives 16.1 g (53.6% of theory) of the title compound.

Workup

  1. filtrationThe resulting precipitate is filtered off with suction
  2. washwashed with water
  3. customdried at 50° C. under reduced pressure overnight

Sources & evidence

ORD record
ord-0123f7d866344191bafad70000e1efc2
Source dataset
uspto-grants-2010_06
Patent number
US07732477B2

Reaction notes

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