Water → Benzyl(cyano)methylamine

HRID 974033Notes

Reaction equation

HRID 974033 reaction equation
[CH3:1][N:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]([NH2:5])=O.C(N(CC)CC)C.O>C(Cl)(Cl)Cl.[OH-].[Na+]>[CH3:1][N:2]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[C:3]#[N:5]

Participants

6

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 156760161-benzyl-1-methylurea

Product 1

HCID 12526219Benzyl(cyano)methylamineYield 82.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 14798Sodium HydroxideSolvent

Procedure

To N-methyl-N-benzylurea (1.64 g, 0.01 mol) in chloroform (24 ml) and 50% aqueous sodium hydroxide solution (5.4 ml) was added triethylamine (0.1 g, 0.001 mol) and the mixture was vigorously stirred at room temperature for 3.5 h. After addition of water and chloroform, the mixture was stirred, then extracted with chloroform. The extracts were washed with water, dried with anhydrous sodium sulfate, and evaporated under reduced pressure to a residue, which was chromatographed to afford N-methyl-N-benzylcyanamide (1.2 g, 82% yield) as oily substance: NMR(CDCl3) δ 2.77(s, 3H), 4.14(s, 2H), 7.25-7.50(m, 5H); IR(neat) 2220, 1495, 1455, 1365, 730 cm-1.

Workup

  1. stirringthe mixture was stirred
  2. extractionextracted with chloroform
  3. washThe extracts were washed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. customevaporated under reduced pressure to a residue, which
  6. customwas chromatographed

Sources & evidence

ORD record
ord-9d6e5cb53c7b48ffaf1563e5c5b55397
Source dataset
uspto-grants-1991_11
Patent number
US05066666

Reaction notes

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