Hydrochloric Acid → Tiafenacil

HRID 215912Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 215912
[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH2:5][NH:6][C:7](=[O:11])[CH:8](Cl)[CH3:9].C(=O)([O-])[O-].[K+].[K+].[Cl:19][C:20]1[C:25]([SH:26])=[CH:24][C:23]([N:27]2[C:32](=[O:33])[CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[N:29]([CH3:38])[C:28]2=[O:39])=[C:22]([F:40])[CH:21]=1.Cl>C(#N)C.C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH2:5][NH:6][C:7](=[O:11])[CH:8]([S:26][C:25]1[CH:24]=[C:23]([N:27]2[C:32](=[O:33])[CH:31]=[C:30]([C:34]([F:36])([F:37])[F:35])[N:29]([CH3:38])[C:28]2=[O:39])[C:22]([F:40])=[CH:21][C:20]=1[Cl:19])[CH3:9]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 186192703-(4-Chloro-2-fluoro-5-sulfanylphenyl)-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dioneHCID 43665913Methyl 3-(2-Chloropropanamido)propanoate

Produkt 1

HCID 67295585TiafenacilAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 3-(2-chloropropionylamino)propionic acid methyl ester (6.93 g) and potassium carbonate (4.72 g) in acetonitrile (150 mL) was added dropwise a solution of 3-(4-chloro-2-fluoro-5-mercaptophenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidin-2,4-dione (11.54 g) in acetonitrile (75 mL) at 45° C. to 50° C. for 1 hour. The reaction mixture was stirred at the same temperature for 2 hours and neutralized at 5° C. with 1 N hydrochloric acid. Water and ethyl acetate were added to separate the organic layer. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried with magnesium sulfate, filtered, concentrated, and recrystallized with ether to give the target compound (13.00 g, yield 78%, white solid).

Aufarbeitung

  1. customto separate the organic layer
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customrecrystallized with ether
  8. customto give the target compound (13.00 g, yield 78%, white solid)

Quellen und Nachweise

ORD-Eintrag
ord-33638db1f95240b6a6e6be9441775615
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193198B2

Notizen zur Reaktion

Wird geladen…