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

HRID 524125

Reaction equation

HRID 524125 reaction equation
[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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-a9d3a0234aba46fa9985c8005c74afbf
Source dataset
uspto-grants-2016_05
Patent number
US09340523B2

Linked notes

Loading…