Sodium → 4-(2-chloro-5-fluorobenzyl)-6-methyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one

HRID 240291

反応式

HRID 240291 の反応式
CO[Na].[Na].[Cl:5][C:6]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:7]=1[CH2:8][NH:9][C:10]([NH:12][N:13]=[C:14]([CH3:19])[C:15](OC)=[O:16])=[S:11]>CO>[Cl:5][C:6]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:7]=1[CH2:8][N:9]1[C:15](=[O:16])[C:14]([CH3:19])=[N:13][NH:12][C:10]1=[S:11]

参加物

5

反応物 3

HCID 5360545SodiumHCID 86654855Methyl 2-(2-(2-chloro-5-fluorobenzylcarbamothioyl)hydrazono)propanoateHCID 178418582HCID 178418582、化合物

生成物 1

HCID 583285444-(2-chloro-5-fluorobenzyl)-6-methyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a solution of MeONa (0.82 M) in methanol (200 mL), freshly prepared from sodium (3.80 g, 165 mmol) and dry methanol (200 mL), was added methyl 2-(2-(2-chloro-5-fluorobenzylcarbamothioyl)hydrazono)propanoate (28, 10.00 g, 31.5 mmol). The mixture was heated at reflux for 36 h. Most of the solvent was evaporated. The resulting residue was diluted with water (300 mL), acidified with 2 N HCl to pH=1˜2, and then extracted with EtOAc (250 mL×2). The extracts were washed with brine, dried over MgSO4, and concentrated to give a mixture, which was separated by silica gel column, and eluted with 20-30% ethyl acetate in petroleum ether to give 4-(2-chloro-5-fluorobenzyl)-6-methyl-3-thioxo-3,4-dihydro-1,2,4-triazin-5(2H)-one (29).

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 36 h
  3. customMost of the solvent was evaporated
  4. additionThe resulting residue was diluted with water (300 mL)
  5. extractionextracted with EtOAc (250 mL×2)
  6. washThe extracts were washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customto give a mixture, which
  10. customwas separated by silica gel column
  11. washeluted with 20-30% ethyl acetate in petroleum ether

出典と根拠

ORDレコード
ord-ef26d88e0aad42ae88e8a23b6ba642bf
出典データセット
uspto-grants-2014_02
特許番号
US08648073B2

関連ノート

読み込み中…