Cyanamide → n'-Cyano-2-(2-methylphenyl)ethanimidamide

HRID 1294701Notes

Reaction equation

HRID 1294701 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10](=[NH:14])OCC.[O-]CC.[Na+].[N:19]#[C:20][NH2:21]>C(O)C>[C:20]([N:21]=[C:10]([NH2:14])[CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH3:2])#[N:19]

Participants

5

Reactant 3

HCID 9864CyanamideHCID 2723922Sodium ethoxideHCID 20076957Ethyl 2-(2-methylphenyl)ethanimidate--hydrogen chloride (1/1)

Product 1

HCID 86093262n'-Cyano-2-(2-methylphenyl)ethanimidamideYield 77.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

A solution of Example 1B (4 g, 18.72 mmol)) in absolute ethanol (50 ml) was treated with a 21% sodium ethoxide solution in ethanol (7 ml, 18.72 mmol) and the precipitated sodium chloride was filtered off. The filtrate was then treated with a solution of cyanamide (0.79 g, 18.72 mmol) in absolute ethanol (25 ml) and stirred at room temperature for one hour. The solvent was evaporated under reduced pressure. The residual oil was triturated with ether to afford white crystals that were filtered and dried to yield 2.5 g of product. MS (ESI+) m/z 174 (M+H)+.

Workup

  1. filtrationthe precipitated sodium chloride was filtered off
  2. customThe solvent was evaporated under reduced pressure
  3. customThe residual oil was triturated with ether
  4. customto afford white crystals that
  5. filtrationwere filtered
  6. customdried

Sources & evidence

ORD record
ord-e5451bc55add4cb4988fb0f70c8e78bf
Source dataset
uspto-grants-2007_07
Patent number
US07241776B2

Reaction notes

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