Methyl iodide → 2-chloro-5-fluorobenzyl-6-methyl-3-(methylthio)-1,2,4-triazin-5(4H)-one

HRID 524125

Reaktionsgleichung

Reaktionsgleichung von HRID 524125
[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:3]=1[CH2:4][N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[N:8][NH:7][C:6]1=[S:13].[CH3:19]I.[OH-].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:3]=1[CH2:4][N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[N:8][N:7]=[C:6]1[S:13][CH3:19]

Komponenten

6

Edukt 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 58328544HCID 58328544, Verbindung

Produkt 1

HCID 583285422-chloro-5-fluorobenzyl-6-methyl-3-(methylthio)-1,2,4-triazin-5(4H)-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a suspension of 4-(2-chloro-5-fluorobenzyl)-6-methyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one (29, 3.06 g, 10.72 mmol) in ethanol (50 mL) was added MeI (2.44 g, 17.1 mmol) followed by NaOH (429 mg, 10.72 mmol). The mixture was stirred at RT for 40 min to produce a clear yellow solution. The reaction was diluted with water (200 mL), and extracted with EtOAc (100 mL×3). The extracts were washed with brine, dried over MgSO4, and concentrated to give the crude product (3.195 g). This was crystallized from ethyl acetate-petroleum ether to give 4-(2-chloro-5-fluorobenzyl)-6-methyl-3-(methylthio)-1,2,4-triazin-5(4H)-one (30). MS: m/z, 300 (100%, M+1), 302 (35%).

Aufarbeitung

  1. customto produce a clear yellow solution
  2. extractionextracted with EtOAc (100 mL×3)
  3. washThe extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give the crude product (3.195 g)
  7. customThis was crystallized from ethyl acetate-petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-a9d3a0234aba46fa9985c8005c74afbf
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340523B2

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