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

HRID 1198661

反応式

HRID 1198661 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.CCOCC>O1CCCC1>[NH2:1][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:17]#[N:18])=[CH:9][CH:10]=1

参加物

6

反応物 4

HCID 962WaterHCID 3283Diethyl EtherHCID 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 4-azidomethyl-2'-cyanobiphenyl (4.68 g, 20 mmole) in 40 ml of dry tetrahydrofuran (THF) was stirred under N2 at room temperature as 5.3 g (20 mmole) of triphenylphosphine was added in small portions over a period of about 10 minutes. After 2 hours, by which time gas evolution had ceased, 532 μl (532 mg, 29.6 mmole) of H2O was added. After an additional 23 hours, the solution was concentrated in vacuo to give a pale golden gum. This material was chromatographed on a column of silica gel (50×8.5 cm) packed in CH2Cl2. The column was eluted with a gradient of 0-6% methanol in CH2Cl2. Concentration of the product fractions gave a foam which solidified upon trituration with ether. This material was collected on a filter, washed further with some ether, and dried in vacuo at 50° C. to give white crystals, of satisfactory purity; mass spectrum (FAB) m/e 209 (M+1)+.

後処理

  1. additionwas added in small portions over a period of about 10 minutes
  2. waitAfter an additional 23 hours
  3. concentrationthe solution was concentrated in vacuo
  4. customto give a pale golden gum
  5. customThis material was chromatographed on a column of silica gel (50×8.5 cm)
  6. washThe column was eluted with a gradient of 0-6% methanol in CH2Cl2
  7. customConcentration of the product fractions gave a foam which
  8. customThis material was collected on a filter
  9. washwashed further with some ether
  10. customdried in vacuo at 50° C.
  11. customto give white crystals

出典と根拠

ORDレコード
ord-481edb139da147e6bc2ccf89d6aca787
出典データセット
uspto-grants-1994_01
特許番号
US05281614

関連ノート

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