Potassium Carbonate → Methyl 5-(2-ethoxy-2-oxoethylamino)-4-nitrothiophene-2-carboxylate

HRID 1184826Notes

Reaction equation

HRID 1184826 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7](Cl)=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)=[O:4].Cl.[CH2:15]([O:17][C:18](=[O:21])[CH2:19][NH2:20])[CH3:16].C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:15]([O:17][C:18](=[O:21])[CH2:19][NH:20][C:7]1[S:6][C:5]([C:3]([O:2][CH3:1])=[O:4])=[CH:9][C:8]=1[N+:10]([O-:12])=[O:11])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 13205564Methyl 5-chloro-4-nitrothiophene-2-carboxylate

Product 1

HCID 67125551Methyl 5-(2-ethoxy-2-oxoethylamino)-4-nitrothiophene-2-carboxylateYield 89.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 5-chloro-4-nitrothiophene-2-carboxylic acid methyl ester (6.03 g, 27.2 mmol), glycine ethyl ester hydrochloride (4.18 g, 29.9 mmol) and potassium carbonate (9.4 g, 68 mmol) in acetonitrile (200 mL) was stirred 4 h at 70° C. Quenched in ice/water. The resulting precipitation was collected by filtration, washed with water and dried to give methyl 5-(2-ethoxy-2-oxoethylamino)-4-nitrothiophene-2-carboxylate 19 (7.02 g, 89%). NMR (400 MHz, CDCl3) 1.35 (t, J=7.0 Hz, 3H), 3.87 (s, 3H), 4.11 (d, J=5.5 Hz, 2H), 4.33 (q, J=14.0 and 7.0 Hz, 2H), 8.04 (s, 1H), 8.75 (br s, 1H). (m/z)=289 (M+H)+.

Workup

  1. customQuenched in ice/water
  2. customThe resulting precipitation
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-28baf1194e5a4fada4479206d13c8b02
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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