Benzaldehyde → N-Benzyl-4-iodoaniline

HRID 2198866Notes

Reaction equation

HRID 2198866 reaction equation
[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

Participants

6

Reactant 3

HCID 240BenzaldehydeHCID 6331BoraneHCID 108934-Iodoaniline

Product 1

HCID 14944691N-Benzyl-4-iodoaniline

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-c338f211e2064813b4976c7419d92d7d
Source dataset
uspto-grants-1982_11
Patent number
US04360511

Reaction notes

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