Diethyl dithiophosphate, potassium salt → Methyl 5-carbamothioyl-2,4-dimethylbenzoate

HRID 541243

Reaktionsgleichung

Reaktionsgleichung von HRID 541243
[C:1]([C:3]1[C:4]([CH3:14])=[CH:5][C:6]([CH3:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2].P(OCC)(OCC)([S-])=[S:16]>O1CCCC1.O>[C:1]([C:3]1[C:4]([CH3:14])=[CH:5][C:6]([CH3:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])(=[S:16])[NH2:2]

Komponenten

4

Edukt 2

HCID 1385274Diethyl dithiophosphate, potassium saltHCID 68288737Methyl 5-cyano-2,4-dimethylbenzoate2×

Produkt 1

HCID 86672528Methyl 5-carbamothioyl-2,4-dimethylbenzoateAusbeute 57,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a round-bottom flask was added a solution of methyl 5-cyano-2,4-dimethylbenzoate (compound 2.3, 1.78 g, 9.41 mmol, 1.00 equiv) in tetrahydrofuran/H2O (30/3 mL). O,O′-diethyl dithiophosphate (3.30 g, 17.7 mmol, 2.00 equiv) was added and the resulting mixture was stirred for 2 days at 85° C. (CAUTION: significant gas evolution occurs—this and all other reactions described herein should be carried out in well ventilated fume hoods). After cooling to ambient temperature, the mixture was extracted with 2×50 mL of ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated in vacuo. The crude residue was purified using silica gel column chromatography with ethyl acetate/petroleum ether (1:10) as eluent to furnish 1.20 g (57%) of the title compound as a yellow solid.

Aufarbeitung

  1. temperatureAfter cooling to ambient temperature
  2. extractionthe mixture was extracted with 2×50 mL of ethyl acetate
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-3b1ae739c03a4a65b263009a446ed7ef
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08871790B2

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