Trichloroacetyl isocyanate → Methyl 5-(4-methoxyphenyl)-2-({[(trichloroacetyl)amino]carbonyl}amino)thiophene-3-carboxylate

HRID 30334

Reaktionsgleichung

Reaktionsgleichung von HRID 30334
[CH3:1][O:2][C:3]([C:5]1[CH:9]=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][CH:11]=2)[S:7][C:6]=1[NH2:18])=[O:4].[Cl:19][C:20]([Cl:27])([Cl:26])[C:21]([N:23]=[C:24]=[O:25])=[O:22]>C1COCC1>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([C:8]2[S:7][C:6]([NH:18][C:24]([NH:23][C:21](=[O:22])[C:20]([Cl:27])([Cl:26])[Cl:19])=[O:25])=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:9]=2)=[CH:11][CH:12]=1

Komponenten

4

Edukt 2

HCID 76400Trichloroacetyl isocyanateHCID 689635672-Amino-5-(4-methoxy-phenyl)-thiophene-3-carboxylic acid methyl ester

Produkt 1

HCID 11546916Methyl 5-(4-methoxyphenyl)-2-({[(trichloroacetyl)amino]carbonyl}amino)thiophene-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-Amino-5-(4-methoxy-phenyl)-thiophene-3-carboxylic acid methyl ester (7.15 g, 27.2 mmol) in anhydrous THF (150 mL) was added trichloroacetyl isocyanate (6.4 mL, 54 mmol) 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 6.9 g (56%) an off-white solid. The product was used in the next step without purification 1H NMR (d6-DMSO δ 12.3, br s, 1H; δ 12.2, s, 1H; δ 7.46, d, 2H; δ 7.32, s, 1H; δ 6.85, d, 2H; δ 3.75, s, 3H; δ 3.66, s, 3H), LC/MS (APCI, ES, M+H=451).

Aufarbeitung

  1. additionAfter the addition
  2. customa precipitate formed

Quellen und Nachweise

ORD-Eintrag
ord-4c864b855fd644c992f4f26b7ed6bdd3
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07423061B2

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