Water → 2-[4-(Aminomethyl)phenyl]benzonitrile

HRID 36179

반응식

HRID 36179 반응식
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]#[N:18])=[CH:7][CH:6]=1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(Cl)Cl>O1CCCC1.CO>[C:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:8]1[CH:7]=[CH:6][C:5]([CH2:4][NH2:1])=[CH:10][CH:9]=1)#[N:18]

참가 물질

7

반응물 4

HCID 962WaterHCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 103539894-Azidomethyl-2'-cyanobiphenyl

생성물 1

HCID 13933412-[4-(Aminomethyl)phenyl]benzonitrile

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 5.85 g (25 mmole) of 4-azidomethyl-2'-cyanobiphenyl (from Step A) in 50 ml of dry tetrahydrofuran was treated portionwise with 6.55 g (25 mmole) of triphenylphospine over 3-4 minutes. The solution was stirred at ambient temperature under N2, and gas evolution proceeded at a moderate rate. A mild exotherm occurred, and the solution was cooled in a water bath as necessary. After 2 hours, by which time gas evolution had ceased, 675 μl (37.5 mmole) of H2O was added, and stirring was continued at room temperature under N2. After 22 hours, the solution was concentrated in vacuo, and the residual oil was chromatographed on a column of silica gel (gradient elution with 2-10% methanol in CH2Cl2). The residue from evaporation of the pooled product fractions was partitioned between ether-CH2Cl2 and saturated Na2CO3 (aqueous). The organic phase was dried (Na2SO4), filtered, and concentrated in vacuo to yield 4.64 g (89%) of air-sensitive, nearly white crystals, mp 54°-55° C., homogeneous by TLC in 9:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 209(M+1)+.

후처리

  1. temperaturethe solution was cooled in a water bath as necessary
  2. stirringstirring
  3. customwas continued at room temperature under N2
  4. waitAfter 22 hours
  5. concentrationthe solution was concentrated in vacuo
  6. customthe residual oil was chromatographed on a column of silica gel (gradient elution with 2-10% methanol in CH2Cl2)
  7. customThe residue from evaporation of the pooled product fractions
  8. customwas partitioned between ether-CH2Cl2 and saturated Na2CO3 (aqueous)
  9. dry with materialThe organic phase was dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto yield 4.64 g (89%) of air-sensitive, nearly white crystals, mp 54°-55° C.

출처 및 근거

ORD 기록
ord-f6a226c931854184ba221b414cc52b10
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05411980

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