Thionyl Chloride → HCID 178509679、化合物

HRID 1198177ノート

反応式

HRID 1198177 の反応式
O[C:2]1([CH:12]([C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=2)[C:13]2[N:17]=[CH:16][NH:15][N:14]=2)[CH:9]2[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:11][CH:3]1[CH2:4]3)[CH2:8]2.S(Cl)(Cl)=O>ClCCl>[CH:3]12[CH2:11][CH:7]3[CH2:6][CH:5]([CH2:10][CH:9]([CH2:8]3)[C:2]1=[C:12]([C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1)[C:13]1[N:17]=[CH:16][NH:15][N:14]=1)[CH2:4]2

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 178509717HCID 178509717、化合物

生成物 1

HCID 178509679HCID 178509679、化合物収率 62.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

9 g of crude 4-[2-hydroxyadamant-2-yl-1-(1,2,4-triazolyl)methyl]benzonitrile is dissolved at 0° in 50 ml of dichloromethane and stirred at 0° with 24 ml of thionyl chloride for 1 hour. Then the mixture is concentrated to dryness in an oil pump vacuum, dissolved in 50 ml of dichloromethane, stirred for 2 hours with 32 ml of triethylamine, diluted with water, extracted three times with ethyl acetate, washed with sodium chloride solution, dried over sodium sulfate, concentrated to dryness under vacuum, and chromatographed on silica gel with hexane/ethyl acetate, yielding 5.3 g of 4-[2-adamantylidene-1-(1,2,4-triazolyl)methyl]benzonitrile as the free base, mp 130°, which is converted with hydrochloric acid into the hydrochloride, mp 105°.

後処理

  1. concentrationThen the mixture is concentrated to dryness in an oil pump vacuum
  2. dissolutiondissolved in 50 ml of dichloromethane
  3. additiondiluted with water
  4. extractionextracted three times with ethyl acetate
  5. washwashed with sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness under vacuum
  8. customchromatographed on silica gel with hexane/ethyl acetate

出典と根拠

ORDレコード
ord-180928644ea348bf93a36eaacb51a740
出典データセット
uspto-grants-1994_01
特許番号
US05280035

反応ノート

読み込み中…