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

HRID 659739

反応式

HRID 659739 の反応式
[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

参加物

6

反応物 3

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

生成物 1

HCID 684435584-(2-Chlorooxazol-5-yl)benzonitrile収率 82%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 22728543Water ethylacetate溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e78b697eaa13435da6d81b1c6f83a030
出典データセット
uspto-grants-2011_12
特許番号
US08080669B2

関連ノート

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