Hexachloroethane → 4-(2-Chlorooxazol-5-yl)benzonitrile

HRID 659739

반응식

HRID 659739 반응식
[O:1]1[C:5]([C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=2)=[CH:4][N:3]=[CH:2]1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Cl:24]C(Cl)(Cl)C(Cl)(Cl)Cl>C1COCC1.CCOC(C)=O.O>[Cl:24][C:2]1[O:1][C:5]([C:6]2[CH:7]=[CH:8][C:9]([C:10]#[N:11])=[CH:12][CH:13]=2)=[CH:4][N:3]=1

참가 물질

6

반응물 3

HCID 6214HexachloroethaneHCID 2733832Lithium HexamethyldisilazideHCID 27772714-(1,3-Oxazol-5-yl)benzonitrile

생성물 1

HCID 684435584-(2-Chlorooxazol-5-yl)benzonitrile수율 82%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 22728543Water ethylacetate용매

반응 조건

온도
-78 °C

실험 절차

To a solution of 4-Oxazol-5-yl-benzonitrile (3 g, 17.65 mmol) in anhydrous THF (80 mL) at −78° C. under an argon atmosphere was slowly added a solution of LiHMDS (21.2 mL, 1 M in THF, 21.2 mmol). After 1 h at −78° C., solid hexachloroethane (6.275 g, 26.48 mmol) was added. The mixture was then stirred at −78° C. for 1 h and allowed to slowly warm to room temperature and stir for 3 h. The reaction was diluted with AcOEt/H2O (50 mL/15 mL). The organic layer was washed with brine, dried with MgSO4 and filtered. After removal of solvent the solid obtained was recrystallize from Hexane to give the title compound as a white solid (2.95 g, 82%). m.p.=144° C.

후처리

  1. temperatureto slowly warm to room temperature
  2. stirringstir for 3 h
  3. washThe organic layer was washed with brine
  4. dry with materialdried with MgSO4
  5. filtrationfiltered
  6. customAfter removal of solvent the solid
  7. customobtained
  8. customwas recrystallize from Hexane

출처 및 근거

ORD 기록
ord-e78b697eaa13435da6d81b1c6f83a030
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080669B2

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