Acetic Acid → 6-Methyl-5-(m-trifluoromethylbenzylmercapto)-pyridine-2-carboxylic acid methyl ester

HRID 2049296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2049296
[H-].[Na+].[F:3][C:4]([F:14])([F:13])[C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8][SH:9].[CH3:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([N+]([O-])=O)=[C:21]([CH3:28])[N:20]=1)=[O:18].C(O)(=O)C>CN(C)C=O>[CH3:15][O:16][C:17]([C:19]1[CH:24]=[CH:23][C:22]([S:9][CH2:8][C:7]2[CH:10]=[CH:11][CH:12]=[C:5]([C:4]([F:13])([F:14])[F:3])[CH:6]=2)=[C:21]([CH3:28])[N:20]=1)=[O:18]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 24758Sodium hydrideHCID 1412363-(Trifluoromethyl)benzyl mercaptanHCID 11839201Methyl 6-methyl-5-nitropicolinate

Produkt 1

HCID 543879406-Methyl-5-(m-trifluoromethylbenzylmercapto)-pyridine-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To the stirred suspension of 1.08 g of sodium hydride in 25 ml of dimethylformamide the solution of 9.0 g of m-trifluoromethylbenzylmercaptan in 50 ml of dimethylformamide is added during 3 minutes and the mixture stirred for 10 minutes. It is combined with 7.75 g of 6-methyl-5-nitropyridine-2-carboxylic acid methyl ester and the whole stirred on the steam bath for 30 minutes and allowed to stand overnight at room temperature. 2 ml of acetic acid are added and the solution is mixed with ice water to produce a dense, grainy precipitate. It is filtered off and recrystallized from isopropanol-diethyl ether, to yield the 6-methyl-5-(m-trifluoromethylbenzylmercapto)-pyridine-2-carboxylic acid methyl ester melting at 91°-93°.

Aufarbeitung

  1. additionis added during 3 minutes
  2. stirringthe whole stirred on the steam bath for 30 minutes
  3. waitto stand overnight at room temperature
  4. customto produce a dense, grainy precipitate
  5. filtrationIt is filtered off
  6. customrecrystallized from isopropanol-diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-207d709df63742fa87431f2eb1ba2c6b
Quelldatensatz
uspto-grants-1980_04
Patentnummer
US04197302

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