Thiomorpholine → 4-(2,6-Difluoro-4-nitrophenyl)thiomorpholine

HRID 395258ノート

反応式

HRID 395258 の反応式
FC(F)(F)S(O[C:7]1[C:12]([F:13])=[CH:11][C:10]([N+:14]([O-:16])=[O:15])=[CH:9][C:8]=1[F:17])(=O)=O.[NH:20]1[CH2:25][CH2:24][S:23][CH2:22][CH2:21]1>O1CCCC1>[F:13][C:12]1[CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=[C:8]([F:17])[C:7]=1[N:20]1[CH2:25][CH2:24][S:23][CH2:22][CH2:21]1

参加物

4

反応物 2

HCID 67164ThiomorpholineHCID 181734322,6-Difluoro-4-nitrophenyl trifluoromethanesulfonate

生成物 1

HCID 120965924-(2,6-Difluoro-4-nitrophenyl)thiomorpholine収率 64%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

2,6-Difluoro-4-nitrophenyl trifluoromethanesulfonate (992 mg, 3.23 mmol) is dissolved in dry tetrahydrofuran (15 mL) and then treated dropwise with thiomorpholine (0.487 mL, 4.85 mmol). The reaction is then heated to reflux (70° C.) under nitrogen for 16 hours. The reaction is then allowed to cool to room temperature, stirring over the weekend (56 hours) under nitrogen. At this time, the reaction is found to be complete by thin layer chromatography. The reaction mixture is concentrated under reduced pressure to yield a yellow solid and then absorbed onto silica gel (25 g). The material is then chromatographed on more silica gel (75 g, packed with hexane), eluting with 5% ethyl acetate/hexane to give 535 mg (64%) of the title compound as a solid, mp: 104-105° C.

後処理

  1. temperatureThe reaction is then heated
  2. temperatureto cool to room temperature
  3. concentrationThe reaction mixture is concentrated under reduced pressure
  4. customto yield a yellow solid
  5. customabsorbed onto silica gel (25 g)
  6. customThe material is then chromatographed on more silica gel (75 g, packed with hexane)
  7. washeluting with 5% ethyl acetate/hexane

出典と根拠

ORDレコード
ord-79b20044058b4eb2b38bd4275049cb9f
出典データセット
uspto-grants-2003_08
特許番号
US06605609B2

反応ノート

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