Ammonium Chloride → ETHYL 2-CHLORO-3-METHYL-4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLATE

HRID 2184705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2184705
[Cl:1][C:2]1[S:6][C:5]([CH:7]=O)=[CH:4][C:3]=1[CH3:9].[CH2:10]([O:12][C:13](=[O:18])[CH2:14][N:15]=[N+]=[N-])[CH3:11].[O-]CC.[NH4+].[Cl-]>C(O)C>[CH2:10]([O:12][C:13]([C:14]1[NH:15][C:4]2[C:3]([CH3:9])=[C:2]([Cl:1])[S:6][C:5]=2[CH:7]=1)=[O:18])[CH3:11]

Komponenten

6

Edukt 4

HCID 25517Ammonium ChlorideHCID 69480Acetic acid, azido-, ethyl esterHCID 1194401-Hydroxyethyl radicalHCID 226102715-Chloro-4-methylthiophene-2-carbaldehyde

Produkt 1

HCID 11521594ETHYL 2-CHLORO-3-METHYL-4H-THIENO[3,2-B]PYRROLE-5-CARBOXYLATE

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

5-Chloro-4-methyl-thiophene-2-carbaldehyde was annulated according to Procedure H (aldehyde and azido-acetic acid ethyl ester was added as ethanol solution (1 M of ester) to −20° C. ethoxide solution; allow to warm to 10° C. over 2 h, 10° C. 2 h; reaction poured into cold saturated aqueous NH4Cl; after ether extraction, acrylate organic phase washed with water until aqueous phase was neutral; solution of crude acrylate added to refluxing xylenes over 5 min and then heated at reflux).

Aufarbeitung

  1. custom2 h
  2. customreaction
  3. extractionafter ether extraction, acrylate organic phase
  4. washwashed with water until aqueous phase
  5. additionsolution of crude acrylate added
  6. temperatureto refluxing xylenes over 5 min
  7. temperatureheated
  8. temperatureat reflux)

Quellen und Nachweise

ORD-Eintrag
ord-66b7a6330b4340e0921337d827350107
Quelldatensatz
uspto-grants-2002_06
Patentnummer
US06399601B1

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