Maleic Acid → HCID 70457145, compound

HRID 1979744Notes

Reaction equation

HRID 1979744 reaction equation
CS([C:4]1[NH:5][CH:6]=[C:7]([CH2:12][CH2:13][CH2:14][CH3:15])[C:8]=1[N+:9]([O-:11])=[O:10])=O.[CH3:16][C:17]1[NH:21][CH:20]=[N:19][C:18]=1[CH2:22][S:23][CH2:24][CH2:25][NH2:26].[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31]>C(O)C.C(O)(C)C>[C:27]([OH:34])(=[O:33])/[CH:28]=[CH:29]\[C:30]([OH:32])=[O:31].[CH3:16][C:17]1[NH:21][CH:20]=[N:19][C:18]=1[CH2:22][S:23][CH2:24][CH2:25][NH:26][C:4]1[NH:5][CH:6]=[C:7]([CH2:12][CH2:13][CH2:14][CH3:15])[C:8]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 3

HCID 444266Maleic AcidHCID 6655684-(((2-Aminoethyl)thio)methyl)-5-methylimidazoleHCID 13646636HCID 13646636, compound

Product 1

HCID 70457145HCID 70457145, compoundYield 9.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 3776IsopropanolSolvent2×

Procedure

2-Methylsulphinyl-3-nitro-4-n-butylpyrrole (2.78 g) was dissolved in ethanol and added to a solution of 2-(5-methyl-4-imidazolylmethylthio)ethylamine (2.08 g) in ethanol (total 100 ml). The mixture was heated under reflux for nine days. The solution was evaporated to dryness, and the residue was chromatographed on a silica gel column using chloroform and ethyl acetate to give 0.65 g of crude product as a brown oil. The crude product was dissolved in isopropanol (30 ml) and reacted with a solution of maleic acid (0.5 g) in 2-propanol. The mixture was warmed on a steam bath for a few minutes and then allowed to cool, yielding bright yellow crystals of 2-[2-(5-methyl-4-imidazolylmethylthio)ethyl]amino-3-nitro-4-n-butylpyrrole maleate (0.19 g), m.p. 94°-95°.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for nine days
  3. customThe solution was evaporated to dryness
  4. customthe residue was chromatographed on a silica gel column
  5. customto give 0.65 g of crude product as a brown oil
  6. temperatureThe mixture was warmed on a steam bath for a few minutes
  7. temperatureto cool

Sources & evidence

ORD record
ord-b7563bd35c9844378bc4d3cc5d463560
Source dataset
uspto-grants-1984_11
Patent number
US04482563

Reaction notes

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