Benzaldehyde → N-Benzyl-4-iodoaniline

HRID 2198866Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2198866
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.B>C(COC)OC.O1CCCC1>[CH2:9]([NH:6][C:5]1[CH:7]=[CH:8][C:2]([I:1])=[CH:3][CH:4]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

6

Edukt 3

HCID 240BenzaldehydeHCID 6331BoraneHCID 108934-Iodoaniline

Produkt 1

HCID 14944691N-Benzyl-4-iodoaniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

2.19 Grams of p-iodoaniline and 1.06 g of benzaldehyde were dissolved in 50 ml of glyme and the resulting solution heated to 60° for two hours. The temperature was maintained for an additional hour after the addition of 30 ml of a 1 M solution of borane in tetrahydrofuran. The excess boron hydride was then destroyed by the addition of about 10 ml of methanol. To this mixture was added 100 ml of a 0.3 M solution of sodium hydroxide and the resulting solution extracted with 100 ml of ether to yield N-benzyl-p-iodoaniline, Rf =0.70.

Aufarbeitung

  1. temperaturethe resulting solution heated to 60° for two hours
  2. temperatureThe temperature was maintained for an additional hour
  3. customThe excess boron hydride was then destroyed by the addition of about 10 ml of methanol
  4. additionTo this mixture was added 100 ml of a 0.3 M solution of sodium hydroxide
  5. extractionthe resulting solution extracted with 100 ml of ether

Quellen und Nachweise

ORD-Eintrag
ord-c338f211e2064813b4976c7419d92d7d
Quelldatensatz
uspto-grants-1982_11
Patentnummer
US04360511

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