Ethanol → dibenzylcyanamide

HRID 390760Notes

Reaction equation

HRID 390760 reaction equation
C([O-])(=O)C.[Na+].[CH2:6]([NH:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(O)C.[N:24]#[C:25]Br>C(Cl)Cl.C1(C)C=CC=CC=1.[OH-].[Na+]>[CH2:14]([N:13]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:25]#[N:24])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 7656DibenzylamineHCID 10476Cyanogen BromideHCID 517045Sodium Acetate

Product 1

HCID 222027dibenzylcyanamideYield 89%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a dry 2 L round bottom flask, equipped with an overhead stirrer, charged: sodium acetate (120 gm), 1 dibenzyl amine (100 gm) and 600 mL of ethanol. To this suspension at room temperature, was added a 3 M solution of cyanogen bromide in methylene chloride over 30 minutes (340 mL). The suspension was allowed to stir at ambient temperature until reaction completion was observed via HPLC. The reaction mixture was diluted with 1 L of toluene and 1 N sodium hydroxide was added over 15 minutes. The reaction mixture was stirred for 1 hour and the layers separated. The organic layer was dried over sodium sulfate, filtered, and concentrated to an oil that solidified upon standing. Recrystallization from a 1:1 2 L mixture of IPE/Heptanes gave 101 g (89%) of product. 1H NMR (400 MHz, CD3OD) 7.42-7.15 (m, 10H), 1.31 (s, 4H). 13C NMR (400 MHz, CD3OD) 135.1, 128.8, 128.7, 128.5, 118.0, 54.6. C, H, N Calculated (found) 81.05 (80.71), 6.35 (6.52), 12.60 (12.65)

Workup

  1. customTo a dry 2 L round bottom flask, equipped with an overhead stirrer
  2. additioncharged
  3. additionwas added over 15 minutes
  4. stirringThe reaction mixture was stirred for 1 hour
  5. customthe layers separated
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to an oil that
  9. customRecrystallization from a 1:1 2 L mixture of IPE/Heptanes

Sources & evidence

ORD record
ord-5a63d15c0aa040ce8f061164829bcf45
Source dataset
uspto-grants-2013_02
Patent number
US08383660B2

Reaction notes

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