Sulfuric Acid → Methyl 4-[2-fluoro-3-(methylsulfonyl)phenyl]piperazine-1-carboxylate

HRID 2358140ノート

反応式

HRID 2358140 の反応式
[F:1][C:2]1[C:7]([S:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:11]1.[O-]O.[OH-:22].[Na+].S(=O)(=O)(O)[OH:25]>[O-][W]([O-])(=O)=O.[Na+].[Na+]>[F:1][C:2]1[C:7]([S:8]([CH3:9])(=[O:25])=[O:22])=[CH:6][CH:5]=[CH:4][C:3]=1[N:10]1[CH2:15][CH2:14][N:13]([C:16]([O:18][CH3:19])=[O:17])[CH2:12][CH2:11]1

参加物

6

反応物 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 18500Perhydroxyl radicalHCID 57448074Methyl 4-[2-fluoro-3-(methylthio)phenyl]piperazine-1-carboxylate

生成物 1

HCID 57448075Methyl 4-[2-fluoro-3-(methylsulfonyl)phenyl]piperazine-1-carboxylate

試薬・触媒・溶媒 1

HCID 26052Sodium tungstate触媒

反応条件

温度
55 °C

実験手順

To an ice cooled solution of methyl 4-[2-fluoro-3-(methylthio)phenyl]piperazine-1-carboxylate (1.4 g, 4.9 mmol) in sulfuric acid (1 M, 10 ml) was added sodium tungstate (0.016 g, 0.05 mmol) in one portion followed by droppwise addition of hydroperoxide (30%, 1.25 ml, 12.2 mmol). The reaction mixture was warmed to 55° C. and was stirred for 20 h. The reaction mixture was brought to ambient temperature and aqueous sodium hydroxide (5 M, 50 ml) was added. The aqueous phase was extracted with ethyl acetate (2×50 ml). The combined organic phase was dried (MgSO4) and evaporated to dryness to give the title compound. Yield (1.1 g). MS m/z (rel. intensity, 70 eV) 316 (M+, 58), 296 (30), 228 (bp), 216 (38), 56 (71).

後処理

  1. customwas brought to ambient temperature
  2. extractionThe aqueous phase was extracted with ethyl acetate (2×50 ml)
  3. dry with materialThe combined organic phase was dried (MgSO4)
  4. customevaporated to dryness

出典と根拠

ORDレコード
ord-9c460f7b015a4477bbab89834c3f88e9
出典データセット
uspto-grants-2010_07
特許番号
US07763639B2

反応ノート

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