Methylamine → Ethyl 4-methyl-2-(N'-methylureido)thiophene-3-carboxylate

HRID 1607520Notes

Reaction equation

HRID 1607520 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH3:12])[C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH2:13]([N:15]([CH2:18]C)CC)C.C(Cl)(Cl)=[O:21].CN>O1CCCC1>[CH3:12][C:5]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]([NH:1][C:13]([NH:15][CH3:18])=[O:21])[S:3][CH:4]=1

Participants

6

Reactant 4

HCID 6329MethylamineHCID 6371PhosgeneHCID 8471TriethylamineHCID 521132Ethyl 2-amino-4-methylthiophene-3-carboxylate

Product 1

HCID 15085569Ethyl 4-methyl-2-(N'-methylureido)thiophene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred ice-cooled solution of ethyl 2-amino-4-methyl-thiophene-3-carboxylate (1,85 g, 10 mmole) and triethyl amine (1,4 ml, 10 mmol) in dry tetrahydrofuran (50 ml) was added dropwise a phosgene solution (11 mmol, in toluene). The mixture was thereafter heated to reflux for 30 min, then cooled to room temperature and exposed to a gaseous stream of methylamine for 5 min. After additional stirring for 15 min, the mixture was filtered and the filtrate was evaporated to give the title compound as white crystals.

Workup

  1. temperatureThe mixture was thereafter heated
  2. temperatureto reflux for 30 min
  3. filtrationthe mixture was filtered
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-da50db23273a4eb0b833d8c5bb1271dc
Source dataset
uspto-grants-1989_09
Patent number
US04866065

Reaction notes

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