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

HRID 395258노트

반응식

HRID 395258 반응식
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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-79b20044058b4eb2b38bd4275049cb9f
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06605609B2

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