Benzonitrile → 7-Chloro-2-methyl-5-phenyl-5H-[1,2,4]triazolo[5,1-a]isoindol-5-amine

HRID 1704642노트

반응식

HRID 1704642 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH3:13])[NH:10][N:9]=2)=[CH:4][CH:3]=1.C([Li])CCC.[C:19](#[N:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[Cl-].[NH4+]>O1CCCC1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[C:8]1=[N:12][C:11]([CH3:13])=[N:10][N:9]1[C:19]2([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH2:26]

참가 물질

7

반응물 4

HCID 7505BenzonitrileHCID 25517Ammonium ChlorideHCID 124680223-(4-Chlorophenyl)-5-methyl-1H-1,2,4-triazoleHCID 178418339Butyllithium

생성물 1

HCID 124680237-Chloro-2-methyl-5-phenyl-5H-[1,2,4]triazolo[5,1-a]isoindol-5-amine수율 49.1%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매2회

실험 절차

2.0 g (10.3 mmol) of 3-(4-Chlorophenyl)-5-methyl-1,2,4-triazole is dissolved in 50 ml of tetrahydrofuran (THF) (freshly distilled from lithium aluminum hydride) mechanically stirred in a 250 ml round-bottom 3-necked flask equipped with a septum and nitrogen inlet and cooled in an ice bath. 13.6 ml (22.7 mmol) of n-butyllithium (1.67 mol/liter in hexane) is injected with a syringe and the mixture is stirred in the ice bath for 30 minutes. 2.12 g (20.6 mmol) of benzonitrile is added in a little THF. After stirring for 30 minutes in the ice bath and for 30 minutes at room temperature, the mixture is poured into a chilled stirred mixture of 100 ml of 2.5 M ammonium chloride and 200 ml of chloroform. The layers are separated and the aqueous layer washed with chloroform. The combined chloroform layers are washed with water and dried (Na2SO4). The chloroform is removed under vacuum and the residue is recrystallized from toluene to yield 1.5 g of the title compound, m.p. 173°-175°.

후처리

  1. distillationfreshly distilled from lithium aluminum hydride)
  2. customequipped with a septum and nitrogen inlet
  3. temperaturecooled in an ice bath
  4. additionthe mixture is poured into a chilled
  5. stirringstirred
  6. customThe layers are separated
  7. washthe aqueous layer washed with chloroform
  8. washThe combined chloroform layers are washed with water
  9. dry with materialdried (Na2SO4)
  10. customThe chloroform is removed under vacuum
  11. customthe residue is recrystallized from toluene

출처 및 근거

ORD 기록
ord-cc4e3e4458054f17850e527cbd215fcd
출처 데이터셋
uspto-grants-1978_11
특허 번호
US04127587

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