Ethanol → 2-(3,4-Dicarbethoxy-2,5-dimethyl-pyrrol-1-yl)amino-4,5-dihydro-1H-imidazole hydrobromide

HRID 1576104Notes

Reaction equation

HRID 1576104 reaction equation
[C:1]([CH:4]([CH:10]([C:16](=O)[CH3:17])[C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:5]([O:7][CH2:8][CH3:9])=[O:6])(=O)[CH3:2].C(O)C.[BrH:22].[NH:23]([C:25]1[NH:26][CH2:27][CH2:28][N:29]=1)[NH2:24]>C(O)(=O)C>[BrH:22].[C:11]([C:10]1[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[C:1]([CH3:2])[N:24]([NH:23][C:25]2[NH:29][CH2:28][CH2:27][N:26]=2)[C:16]=1[CH3:17])([O:13][CH2:14][CH3:15])=[O:12]

Participants

5

Reactant 3

HCID 702EthanolHCID 953991,4-Diethyl 2,3-diacetylbutanedioateHCID 30850992-Hydrazino-delta-2-imidazoline hydrobromide

Product 1

HCID 131261452-(3,4-Dicarbethoxy-2,5-dimethyl-pyrrol-1-yl)amino-4,5-dihydro-1H-imidazole hydrobromide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 15 g. (0.0581 mole) of diethyl 2,3-diacetylsuccinate in 150 ml. of absolute ethanol, 1.2 ml. of glacial acetic acid is added. The mixture is gently refluxed for 5 minutes then 8.13 g. (0.0467 mole) of 2-hydrazino-4,5-dihydro-1H-imidazole hydrobromide is added. The mixture is refluxed for 20 hours, then the solvent is evaporated off. The obtained residue is recrystallized several times from isopropanol, and 6.3 g. of the title compound are recovered. M.p. 172°-4°C.

Workup

  1. temperatureThe mixture is gently refluxed for 5 minutes
  2. temperatureThe mixture is refluxed for 20 hours
  3. customthe solvent is evaporated off
  4. customThe obtained residue is recrystallized several times from isopropanol, and 6.3 g
  5. customof the title compound are recovered

Sources & evidence

ORD record
ord-0b7d0294b53349e0b66cb056dc3eec72
Source dataset
uspto-grants-1976_09
Patent number
US03979408

Reaction notes

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