Acetic Acid → Methyl 6-cyanobenzo[b]thiophene-2-carboxylate

HRID 15427

Reaktionsgleichung

Reaktionsgleichung von HRID 15427
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([N+]([O-])=O)[CH:4]=1)#[N:2].[SH:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].C(N(CC)CC)C.C(O)(=O)C>CS(C)=O>[CH3:19][O:18][C:16]([C:15]1[S:14][C:5]2[CH:4]=[C:3]([C:1]#[N:2])[CH:10]=[CH:9][C:6]=2[CH:7]=1)=[O:17]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 132385504-Formyl-3-nitrobenzonitrile

Produkt 1

HCID 11031280Methyl 6-cyanobenzo[b]thiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Versuchsvorschrift

4.08 g (23.2 mmol) of 4-cyano-2-nitrobenzaldehyde, 2.46 g (23.2 mmol) of methyl mercaptoacetate and 6.46 ml (46.4 mmol) of triethylamine in 12.3 ml of DMSO are heated at 80° C. for 2.5 h. The reaction solution is poured into 400 ml of ice-water. After addition of 4 ml of acetic acid, the resulting precipitate is filtered off with suction, washed twice with water and dried at 50° C. under reduced pressure overnight. This gives 4.19 g (83.2% of theory) of the title compound.

Aufarbeitung

  1. filtrationthe resulting precipitate is filtered off with suction
  2. washwashed twice with water
  3. customdried at 50° C. under reduced pressure overnight

Quellen und Nachweise

ORD-Eintrag
ord-1a82eeaf1a20452689323b89dcd1d2e5
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07732477B2

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