15-Crown-5 → HCID 18922255, 화합물

HRID 1289632노트

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HRID 1289632 반응식
[Na].[CH3:2][N:3]1[S:7](=[O:9])(=[O:8])[NH:6][C:5](=[O:10])[CH:4]1[CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14].[F:16][C:17]1[N:22]=[C:21]([F:23])[C:20]([F:24])=[C:19](F)[C:18]=1[F:26].C1OCCOCCOCCOCCOC1>C(#N)C>[F:23][C:21]1[C:20]([F:24])=[C:19]([N:6]2[C:5](=[O:10])[CH:4]([CH2:11][CH2:12][CH:13]([CH3:15])[CH3:14])[N:3]([CH3:2])[S:7]2(=[O:9])=[O:8])[C:18]([F:26])=[C:17]([F:16])[N:22]=1

참가 물질

6

반응물 4

HCID 3633615-Crown-5HCID 69690PentafluoropyridineHCID 5360545SodiumHCID 189222624-(3-Methylbutyl)-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

생성물 1

HCID 18922255HCID 18922255, 화합물수율 41%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a mixture of the sodium salt of 5-methyl-4-(3-methylbutyl)-1,2,5-thiadiazolidin-3-one 1,1-dioxide (1 g; 4.13 mmol, prepared by treatment with sodium methoxide), pentafluoropyridine (0.54 ml, 4.97 mmol), and 0.91 g (4.13 mmol) of 15-Crown-5 suspended in 30 ml of acetonitrile was refluxed for 17 hours. The mixture was cooled, concentrated in vacuo, and the residue extracted with methylene chloride, and the organic layer was washed with water (3×) and brine. After drying over sodium sulfate, the organic layer was concentrated in vacuo and a crude product was purified by flash chromatography (10% ethyl acetate in hexane) to afford 0.62 g (41%) of 2-(2,3,5,6-tetrafluoro-4-pyridyl)-5-methyl-4-(3-methylbutyl)-1,2,5-thiadiazolidin-3-one 1,1-dioxide. (Formula I: R1 =(CH2)2 CH(CH3)2 ; R2 =H; R3 =CH3), as a solid, m.p. 80.5°-81.5° C.

후처리

  1. temperaturewas refluxed for 17 hours
  2. temperatureThe mixture was cooled
  3. concentrationconcentrated in vacuo
  4. extractionthe residue extracted with methylene chloride
  5. washthe organic layer was washed with water (3×) and brine
  6. dry with materialAfter drying over sodium sulfate
  7. concentrationthe organic layer was concentrated in vacuo
  8. customa crude product was purified by flash chromatography (10% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-652bc5a8c01747fa9c48a3dac9a9548c
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05750546

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