Cyanamide → Ethyl n-cyano-2-(2-methylphenyl)ethanimidoate

HRID 1294706Notes

Reaction equation

HRID 1294706 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])[O:11][CH2:12][CH3:13].[N:15]#[C:16]N>C(O)C.CCOCC>[C:16]([N:14]=[C:10]([O:11][CH2:12][CH3:13])[CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[CH3:2])#[N:15]

Participants

5

Reactant 2

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

Product 1

HCID 86093122Ethyl n-cyano-2-(2-methylphenyl)ethanimidoateYield 71.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of Example 26A (15 g, 70.2 mmol) in absolute ethanol (200 mL) was treated with a solution of cyanamide (2.95 g, 70.2 mmol) in dry ether (40 mL) and stirred at room temperature for 72 h. The resulting precipitate was filtered and the solution was concentrated to dryness under reduced pressure to give 10.2 g of the title compound.

Workup

  1. filtrationThe resulting precipitate was filtered
  2. concentrationthe solution was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-66848e15c80e427d9635cf279a7b78fe
Source dataset
uspto-grants-2007_07
Patent number
US07241776B2

Reaction notes

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