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

HRID 240280

반응식

HRID 240280 반응식
[Br: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].[OH-].[Na+].[CH3:21]I>C(O)C.O>[Br: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][CH3:21]

참가 물질

6

반응물 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 58328543HCID 58328543, 화합물

생성물 1

HCID 583285304-(2-bromo-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-bromo-5-fluorobenzyl)-6-methyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one (16, 914 mg, 2.77 mmol) in ethanol (15 mL) was added NaOH (111 mg, 2.77 mmol) followed by MeI (787 mg, 5.54 mmol). The mixture was stirred at RT for 10 min to produce a clear yellow solution. The reaction was diluted with water (100 mL), and extracted with EtOAc (30 mL×2). The extracts were washed with brine, dried over MgSO4 and concentrated to give the crude product. This was purified by silica gel column, and eluted with 20-25% ethyl acetate in petroleum ether to give 4-(2-bromo-5-fluorobenzyl)-6-methyl-3-(methylthio)-1,2,4-triazin-5(4H)-one (17). 1H NMR (400 MHz, DMSO, ppm): δ 7.73 (m, 1H), 7.16 (br, 1H), 7.05 (d, 1H), 5.09 (s, 2H), 2.56 (s, 3H), 2.32 (s, 3H). MS: m/z, 344 (100%, M+1), 346 (100%).

후처리

  1. customto produce a clear yellow solution
  2. extractionextracted with EtOAc (30 mL×2)
  3. washThe extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give the crude product
  7. customThis was purified by silica gel column
  8. washeluted with 20-25% ethyl acetate in petroleum ether

출처 및 근거

ORD 기록
ord-40c9a72703134179a5183d841b46c083
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08648073B2

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