N-cyclopropylurea → HCID 86704350, compound

HRID 1507620

Reaction equation

HRID 1507620 reaction equation
[CH:1]1([NH:4][C:5]([NH2:7])=[O:6])[CH2:3][CH2:2]1.Cl.[NH2:9][C:10](OCC)=[CH:11][C:12](OCC)=[O:13].CC[O-].[Na+]>C(O)C>[NH2:9][C:10]1[NH:7][C:5](=[O:6])[N:4]([CH:1]2[CH2:3][CH2:2]2)[C:12](=[O:13])[CH:11]=1

Participants

5

Reactant 3

HCID 272626N-cyclopropylureaHCID 2723922Sodium ethoxideHCID 53395434Ethyl beta-amino-beta-ethoxyacrylate hydrochloride

Product 1

HCID 86704350HCID 86704350, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of cyclopropyl urea (10 g, 100 mmol, 1 eq) and ethyl 3-amino-3-ethoxy-acrylate HCl (19.55 g, 100 mmol, 1 eq) in Ethanol (125 ml) was heated at 75° C. for 2 hours. To this solution was added 2 equivalents of NaOEt then heated for an additional one hour. Solvent was evaporated, water (50 ml) was added then acidified via concentrated HCl to pH of 4-5. The resulting precipitate was obtained by filtration and washed with cold water to give the desired product (9.35 g, 56%) after vacuum dried overnight at 40° C.: The desired isomer was determined via 2D-NMR; 1H NMR (400 MHz, DMSO-d6) δ 10.18 (1H), 6.10 (2H), 4.44 (1H), 2.38 (1H), 0.85 (2H), 0.62 (2H); m/z (ES+) 168.17

Workup

  1. temperaturethen heated for an additional one hour
  2. customSolvent was evaporated
  3. additionwater (50 ml) was added
  4. customThe resulting precipitate was obtained by filtration
  5. washwashed with cold water

Sources & evidence

ORD record
ord-a26f25c2d3b0437ca122b67ffff123c9
Source dataset
uspto-grants-2015_12
Patent number
US09221821B2

Linked notes

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