Ethyl 3-ethoxy-3-iminopropionate hydrochloride → HCID 4915529, compound

HRID 2377854Notes

Reaction equation

HRID 2377854 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[NH2:12])[C:5]([O:7][CH3:8])=[O:6].Cl.[CH2:14]([O:16][C:17](=[O:24])[CH2:18][C:19](OCC)=N)[CH3:15]>CCO>[CH3:8][O:7][C:5]([C:4]1[CH:9]=[CH:10][C:11]2[N:12]=[C:19]([CH2:18][C:17]([O:16][CH2:14][CH3:15])=[O:24])[NH:1][C:2]=2[CH:3]=1)=[O:6]

Participants

4

Reactant 2

HCID 75345Ethyl 3-ethoxy-3-iminopropionate hydrochlorideHCID 1355243,5-Diamino-2-methylbenzoic acid

Product 1

HCID 4915529HCID 4915529, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 3,4-diaminobenzoate (1 equivalent), was stirred with ethyl-3-ethoxy-3-iminopropanoate hydrochloride (2 equivalents) in EtOH at 70° C. overnight. The reaction mixture was cooled to room temperature, and the EtOH was removed under reduced pressure. The residue was taken up in water and extracted with CH2Cl2 (3×). The organic extracts were dried over Na2SO4, and the solvent was removed. The solid was triturated with Et2O to yield the desired ethyl 2-[5-(methoxycarbonyl)-benzimidazol-2-yl]acetate as an off-white solid. LC/MS m/z: 263.2 (MH+), Rt 1.80 minutes.

Workup

  1. customthe EtOH was removed under reduced pressure
  2. extractionextracted with CH2Cl2 (3×)
  3. dry with materialThe organic extracts were dried over Na2SO4
  4. customthe solvent was removed
  5. customThe solid was triturated with Et2O

Sources & evidence

ORD record
ord-152146edda5749f3ba0be6180f58ae19
Source dataset
uspto-grants-2008_12
Patent number
US07470709B2

Reaction notes

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