Methyl 3-amino-2-thiophenecarboxylate → HCID 5178717, compound

HRID 902501Notes

Reaction equation

HRID 902501 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH2:10])=[O:4]>C(CC(OC)=O)#N>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][C:3](=[O:2])[CH2:5][C:9]#[N:10])=[O:4]

Participants

3

Reactant 1

HCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 5178717HCID 5178717, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 7747Methyl cyanoacetateSolvent

Procedure

A solution of methyl-3-amino-thiophene-2-carboxylate (13 g, 82.70 mmol) in neat methyl cyanoacetate (40 mL) was heated at 210° C. for 10 h. The solution was cooled and excess methyl cyanoacetate was distilled off under vacuum. The residue was taken in methanol, sonicated briefly, and filtered. The solids were washed by cold methanol and dried to yield 9.3 g (50%) of 3-(2-cyano-acetylamino)-thiophene-2-carboxylic acid methyl ester as white solids. MP 146° C.; 1H NMR (400 MHz, DMSO-d6) δ 4.18 (s, 2H), 7.86 (d, J=5.2 Hz, 1H), 7.93 (d, J=5.2 Hz, 1H), 10.25 (s, 1H) ppm; MS m/z=225 amu (M++1).

Workup

  1. temperatureThe solution was cooled
  2. distillationexcess methyl cyanoacetate was distilled off under vacuum
  3. customsonicated briefly
  4. filtrationfiltered
  5. washThe solids were washed by cold methanol
  6. customdried

Sources & evidence

ORD record
ord-d744d1e5b27446b5b3e6125be36e4561
Source dataset
uspto-grants-2008_04
Patent number
US07365200B2

Reaction notes

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