Thionyl Chloride → HCID 178509679, 화합물

HRID 1198177

반응식

HRID 1198177 반응식
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

참가 물질

4

반응물 2

HCID 24386Thionyl ChlorideHCID 178509717HCID 178509717, 화합물

생성물 1

HCID 178509679HCID 178509679, 화합물수율 62.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-180928644ea348bf93a36eaacb51a740
출처 데이터셋
uspto-grants-1994_01
특허 번호
US05280035

연결된 노트

불러오는 중…