Potassium Carbonate → Methyl 5-(2,4-dimethoxybenzylamino)-4-nitrothiophene-2-carboxylate

HRID 1184894Notes

Reaction equation

HRID 1184894 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH2:6].Cl[C:14]1[S:18][C:17]([C:19]([O:21][CH3:22])=[O:20])=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][O:2][C:3]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[CH:7][C:4]=1[CH2:5][NH:6][C:14]1[S:18][C:17]([C:19]([O:21][CH3:22])=[O:20])=[CH:16][C:15]=1[N+:23]([O-:25])=[O:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5972502,4-DimethoxybenzylamineHCID 13205564Methyl 5-chloro-4-nitrothiophene-2-carboxylate

Product 1

HCID 67125578Methyl 5-(2,4-dimethoxybenzylamino)-4-nitrothiophene-2-carboxylateYield 97.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2,4-dimethoxybenzylamine (58.7 mmol, 8.81 ml, 9.81 g), methyl 5-chloro-4-nitrothiophene-2-carboxylate (45.1 mmol, 10 g) and potassium carbonate (180 mmol, 24.94 g) were stirred at rt in Acetonitrile (226 mL) for 1 h. Reaction was quenched with water and the resulting precipitate was collected to give methyl 5-(2,4-dimethoxybenzylamino)-4-nitrothiophene-2-carboxylate 86 (15.5 g, 97%). NMR (400 MHz, CDCl3) 3.82 (s, 3H), 3.85 (s, 3H), 3.86 (s, 3H), 4.45 (d, J=5.9 Hz, 2H), 6.46 (dd, J=8.2 Hz and 2.3 Hz, 1H), 6.50 (d, J=2.3 Hz, 1H), 7.20 (d, J=8.2 Hz, 1H), 7.99 (s, 1H), 8.89 (br s, 1). (m/z)=353 (M+H)+.

Workup

  1. customReaction
  2. customwas quenched with water
  3. customthe resulting precipitate was collected

Sources & evidence

ORD record
ord-78463bcc90fa4ee087ad8ced08ab97a6
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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