Ammonia → 2-Cyclopropyl-2-ethoxycarbonylacetamidine hydrochloride

HRID 1450079Notes

Reaction equation

HRID 1450079 reaction equation
[C:1]([CH:3]([CH:9]1[CH2:11][CH2:10]1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[ClH:12].[NH3:13]>C(O)C>[ClH:12].[CH:9]1([CH:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:1]([NH2:13])=[NH:2])[CH2:10][CH2:11]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 10606956Ethyl 2-cyano-2-cyclopropylacetate

Product 1

HCID 196914032-Cyclopropyl-2-ethoxycarbonylacetamidine hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent3×

Procedure

Into a stirred solution of 38.72 g (0.253 mol) of ethyl 2-cyano-2-cyclopropylacetate (preparation described by R. W. J. Carney and J. Wojtkunski, Org. Prep. Proced. Int., 5, 25 (1973)) in 17.7 mL (0.303 mol) of anhydrous ethanol under a dry N2 atmosphere was introduced 10.0 g (0.274 mol) of gaseous hydrogen chloride with ice cooling. The mixture was allowed to warm to room temperature and stand for 72 hours. The reaction was diluted with 100 mL of anhydrous ethanol, 70 mL of ammonia in ethanol (4.17M) was added slowly at room temperature and the reaction was stirred for 3 hours. The reaction mixture was filtered to remove the ammonium chloride, and the solvent was removed to afford the title compound as a viscous off-white oil, which was taken directly to the next step.

Workup

  1. additionwas added slowly at room temperature
  2. filtrationThe reaction mixture was filtered
  3. customto remove the ammonium chloride
  4. customthe solvent was removed

Sources & evidence

ORD record
ord-6aaf40e4a7a149898bdc16af7e1b83ee
Source dataset
uspto-grants-1997_02
Patent number
US05599816

Reaction notes

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