Trichloroacetyl isocyanate → Methyl 2-({[(trichloroacetyl)amino]carbonyl}amino)thiophene-3-carboxylate

HRID 30344

Reaction equation

HRID 30344 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[CH:8][S:7][C:6]=1[NH2:10])=[O:4].[Cl:11][C:12]([Cl:19])([Cl:18])[C:13]([N:15]=[C:16]=[O:17])=[O:14]>C1COCC1>[Cl:11][C:12]([Cl:19])([Cl:18])[C:13]([NH:15][C:16]([NH:10][C:6]1[S:7][CH:8]=[CH:9][C:5]=1[C:3]([O:2][CH3:1])=[O:4])=[O:17])=[O:14]

Participants

4

Reactant 2

HCID 76400Trichloroacetyl isocyanateHCID 78381Methyl 2-amino-3-thenoate

Product 1

HCID 59789494Methyl 2-({[(trichloroacetyl)amino]carbonyl}amino)thiophene-3-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-amino-thiophene-3-carboxylic acid methyl ester (1 eq) in anhydrous THF (mL) was added trichloroacetyl isocyanate (1 eq) slowly over a period of 5 min. After the addition was complete, a precipitate formed and the reaction stirred for an additional 1 h. The desired product was obtained by filtration to give methyl 2-({[(trichloroacetyl)amino]carbonyl}amino)thiophene-3-carboxylate (99%) as an off-white solid. The product was used in the next step without any further purification. LC/MS (ES, M+H=345).

Workup

  1. additionAfter the addition
  2. customa precipitate formed

Sources & evidence

ORD record
ord-c9ad578238324991a9f7cd8df5c4dd1c
Source dataset
uspto-grants-2008_09
Patent number
US07423061B2

Linked notes

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