Ethyl 3-ethoxy-3-iminopropionate hydrochloride → HCID 178470778, compound

HRID 412701Notes

Reaction equation

HRID 412701 reaction equation
[ClH:1].[NH2:2][C:3]1[CH:4]=[C:5]([NH:10][C:11]([NH2:13])=[NH:12])[CH:6]=[CH:7][C:8]=1[NH2:9].Cl.[CH2:15]([O:17][C:18](=[O:25])[CH2:19][C:20](OCC)=N)[CH3:16]>C(O)(=O)C>[ClH:1].[NH:10]([C:5]1[CH:6]=[CH:7][C:8]2[NH:9][C:20]([CH2:19][C:18]([O:17][CH2:15][CH3:16])=[O:25])=[N:2][C:3]=2[CH:4]=1)[C:11]([NH2:13])=[NH:12]

Participants

4

Reactant 2

HCID 75345Ethyl 3-ethoxy-3-iminopropionate hydrochlorideHCID 178479388HCID 178479388, compound

Product 1

HCID 178470778HCID 178470778, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture comprising N-(3,4-diaminophenyl)guanidine hydrochloride (9.9 g, 49 mmol), ethoxycarbonimidoylacetic acid ethyl ester hydrochloride (12.4 g, 59 mmol) and acetic acid (20 mL) was heated in an oil bath at 110° C. and stirred for 1.5 hours, cooled to room temperature and concentrated in vacuo. The residue was dissolved in ethanol (15 mL) and then ethyl acetate (10 mL) was added to the solution to give a precipitate in suspension. The suspension was filtered and an excess of ethyl ether was added to the filtrate to give a second precipitate. The precipitate was collected by filtration, washed with additional ethyl ether and dried in vacuo to provide ethyl 5-guanidino-1H-benzoimidazol-2-ylacetate hydrochloride (14.1 g, 94% yield) as an off white solid; 1H-NMR (300 MHz, DMSO-d6): 10.2 (s), 7.8 (d), 7.7 (m), 7.3 (d), 4.5 (s), 4.2 (q), 1.2 (t).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe residue was dissolved in ethanol (15 mL)
  3. additionethyl acetate (10 mL) was added to the solution
  4. customto give a precipitate in suspension
  5. filtrationThe suspension was filtered
  6. additionan excess of ethyl ether was added to the filtrate
  7. customto give a second precipitate
  8. filtrationThe precipitate was collected by filtration
  9. washwashed with additional ethyl ether
  10. customdried in vacuo

Sources & evidence

ORD record
ord-b2f24a3ee6f44962a83b689b76c7f2ee
Source dataset
uspto-grants-2003_05
Patent number
US06562854B2

Reaction notes

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