Triethylamine → Methyl 4-(ethoxycarbonylamino)-thiophene-3-carboxylate

HRID 1782695Notes

Reaction equation

HRID 1782695 reaction equation
Cl.[NH2:2][C:3]1[C:4]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][S:6][CH:7]=1.C(N(CC)CC)C.[C:19](Cl)(=[O:23])[O:20][CH2:21][CH3:22]>C1(C)C=CC=CC=1>[CH2:21]([O:20][C:19]([NH:2][C:3]1[C:4]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][S:6][CH:7]=1)=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 2777609Methyl 4-aminothiophene-3-carboxylate Hydrochloride

Product 1

HCID 14328004Methyl 4-(ethoxycarbonylamino)-thiophene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 50.0 g (0.258 mol) of methyl 4-aminothiophen-3-carboxylate-hydrochloride, 700 ml of toluene, 26 g (0.257 mol) of triethylamine and 27 ml (0.283 mol) of ethyl chlorocarbonate was refluxed for 5 hours. The insoluble matter was filtered off, the filtrate was evaporated down in vacuo and the residue was crystallised from petroleum ether. 59.0 g (99.8% of theory) of colourless crystals of melting point 52° C. were obtained.

Workup

  1. temperaturewas refluxed for 5 hours
  2. filtrationThe insoluble matter was filtered off
  3. customthe filtrate was evaporated down in vacuo
  4. customthe residue was crystallised from petroleum ether
  5. custom59.0 g (99.8% of theory) of colourless crystals of melting point 52° C. were obtained

Sources & evidence

ORD record
ord-4dee884051634d85978fb60409e5c8dd
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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