Triethylamine → Methyl 4-nitro-1-benzothiophene-2-carboxylate

HRID 658159Notes

Reaction equation

HRID 658159 reaction equation
[N+]([C:4]1[CH:11]=[CH:10][CH:9]=[C:8]([N+:12]([O-:14])=[O:13])[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>[N+:12]([C:8]1[C:5]2[CH:6]=[C:16]([C:17]([O:19][CH3:20])=[O:18])[S:15][C:4]=2[CH:11]=[CH:10][CH:9]=1)([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 690732,6-Dinitrobenzaldehyde

Product 1

HCID 59341424Methyl 4-nitro-1-benzothiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1.0 g (5.10 mmol) of 2,6-dinitrobenzaldehyde, 0.54 g (5.10 mmol) of methyl mercaptoacetate and 1.42 ml (10.20 mmol) of triethylamine in 3 ml of DMSO are heated at 80° C. for 3.5 h. The reaction solution is poured into 100 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 1.10 g (88.7% 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-a7f71b4dc1ed40b78da3a168703c14b0
Source dataset
uspto-grants-2011_12
Patent number
US08076355B2

Reaction notes

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