Ethyl chloroformate → Methyl 3-((ethoxycarbonyl)amino)thiophene-2-carboxylate

HRID 1422979Notes

Reaction equation

HRID 1422979 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([O-])([O-])=O.[K+].[K+].Cl[C:18]([O:20][CH2:21][CH3:22])=[O:19]>C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[NH:10][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:4]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 11430Potassium CarbonateHCID 89652Methyl 3-amino-2-thiophenecarboxylate

Product 1

HCID 840181Methyl 3-((ethoxycarbonyl)amino)thiophene-2-carboxylateYield 98.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 3-amino-thiophene-2-carboxylic acid methyl ester (2.39 g, 15.2 mmol) in benzene (51 mL) was added K2CO3(6.30 g, 45.6 mmol) followed by ethyl chloroformate (1.74 mL, 18.2 mmol). After heating at reflux for 12 h, the mixture was filtered and the filtrate was concentrated to afford the desired product (3.43 g), which was used in the next step without further purification. MS: 230.0. 1H NMR (400 MHz, CD3OD) δ ppm 7.82 (d, J=5.5 Hz, 1H), 7.66 (d, J=5.6 Hz, 1H), 4.23 (q, J=7.1, Hz, 2H), 3.86 (s, 3H), 1.32 (t, J=7.1 Hz, 3H).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 12 h
  3. filtrationthe mixture was filtered
  4. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-cfe6092098f34a9a8a3d2ac0b2747d71
Source dataset
uspto-grants-2015_01
Patent number
US08927555B2

Reaction notes

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