Propylamine → HCID 69964205, compound

HRID 1357555Notes

Reaction equation

HRID 1357555 reaction equation
[NH2:1][CH:2]([C:6]#[N:7])[C:3]([NH2:5])=[O:4].Cl.[C:9](=[NH:14])(OCC)[CH3:10].[CH2:15](N)[CH2:16][CH3:17]>C(#N)C>[NH2:7][C:6]1[N:14]([CH2:15][CH2:16][CH3:17])[C:9]([CH3:10])=[N:1][C:2]=1[C:3]([NH2:5])=[O:4]

Participants

5

Reactant 3

HCID 7852PropylamineHCID 983412-Amino-2-cyanoacetamideHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)

Product 1

HCID 69964205HCID 69964205, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-amino-2-cyanoacetamide (prepared as described in WO 94/00453; 3.6 g, 36.4 mmol) and ethyl acetimidate hydrochloride (4.50 g, 36.4 mmol) in acetonitrile (85 mL) was stirred at 50° C. for an hour, then cooled to 0° C., and stirred for a further hour. The reaction mixture was filtered, and n-propylamine (3.02 mL, 36.4 mmol) added. The solution was stirred at room temperature for an hour, and left to stand for a further 16 hours. The resulting precipitate was filtered, washed with acetonitrile, then dichloromethane and dried under vacuum to afford the title compound as a solid (3.0 g, 45%).

Workup

  1. temperaturecooled to 0° C.
  2. stirringstirred for a further hour
  3. filtrationThe reaction mixture was filtered
  4. stirringThe solution was stirred at room temperature for an hour
  5. waitleft
  6. filtrationThe resulting precipitate was filtered
  7. washwashed with acetonitrile
  8. dry with materialdichloromethane and dried under vacuum

Sources & evidence

ORD record
ord-10d1fa5145b744b89efc517d43bea513
Source dataset
uspto-grants-2003_07
Patent number
US06593332B2

Reaction notes

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