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

HRID 1198665ノート

反応式

HRID 1198665 の反応式
[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>O1CCCC1>[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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 the title compound as 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)+.

後処理

  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

出典と根拠

ORDレコード
ord-e362b23e313e4b809ee29f2acac7dd61
出典データセット
uspto-grants-1994_01
特許番号
US05281614

反応ノート

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