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

HRID 524125

반응식

HRID 524125 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-a9d3a0234aba46fa9985c8005c74afbf
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09340523B2

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