Dibenzylamine → n,n-Dibenzylformamide

HRID 26585

Reaction equation

HRID 26585 reaction equation
[CH2:1]([NH:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:16](OC(=O)C)(=[O:18])C>C(O)=O>[CH:16]([N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:18]

Participants

4

Reactant 2

HCID 7656DibenzylamineHCID 7918Acetic Anhydride

Product 1

HCID 221415n,n-Dibenzylformamide

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

To an ice-cold and vigorously stirred solution of dibenzylamine (918 g.) in 98% formic acid (105 ml.) is added dropwise, over 45 minutes, acetic anhydride (35 ml.). The resulting mixture is stirred for one hour at room temperature, then diluted with ice water (40 ml.) and kept overnight at 15° C. The solution is evaporated in vacuo to dryness and the residue extracted with ether. The ethereal solution is washed with water, dried over magnesium sulfate, filtered, and evaporated in vacuo to yield N-formyl-dibenzylamine (9.9 g.) as a white solid, m.p. 53°-54.5° C.

Workup

  1. waitkept overnight at 15° C
  2. customThe solution is evaporated in vacuo to dryness
  3. extractionthe residue extracted with ether
  4. washThe ethereal solution is washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-03a6fa7a7c6147029957a8734a984a23
Source dataset
uspto-grants-1979_04
Patent number
US04150223

Linked notes

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