2-Methylimidazole → HCID 10403745, compound

HRID 986531Notes

Reaction equation

HRID 986531 reaction equation
[H-].[Na+].[CH3:3][C:4]1[NH:5][CH:6]=[CH:7][N:8]=1.S(C1C=CC(C)=CC=1)(O[CH2:13][C@@H:14]1[CH2:28][C@H:27]2[C@@H:17]([CH2:18][C:19]3[C:29]4[C:22](=[CH:23][CH:24]=[CH:25][C:26]2=4)[NH:21][CH:20]=3)[N:16]([CH3:30])[CH2:15]1)(=O)=O>CN(C)C=O>[CH3:3][C:4]1[N:5]([CH2:13][C@@H:14]2[CH2:28][C@H:27]3[C@@H:17]([CH2:18][C:19]4[C:29]5[C:22](=[CH:23][CH:24]=[CH:25][C:26]3=5)[NH:21][CH:20]=4)[N:16]([CH3:30])[CH2:15]2)[CH:6]=[CH:7][N:8]=1

Participants

5

Reactant 3

HCID 127492-MethylimidazoleHCID 24758Sodium hydrideHCID 139330156-Methylergolin-8beta-ylmethyl tosylate

Product 1

HCID 10403745HCID 10403745, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.8 g of 50% sodium hydride in an oil was added in small portions to a mixture of 1.2 g of 2-methylimidazole and 16 ml of dimethylformamide, and the resulting mixture was stirred for 30 minutes. 2.0 g of 6-methylergolin-8β-ylmethyl tosylate was added to the mixture which was then heated on a water bath for 3 hours. After allowing the mixture to cool, ice-water was added to the reaction mixture, and the precipitated crystals were separated by filtration, washed with water and purified by silica gel column chromatography (eluted with chloroform). The product was recrystallized from ethanol to obtain 1.1 g of the titled compound as colorless needles having a melting point higher than 300° C. (with decomposition).

Workup

  1. temperaturewas then heated on a water bath for 3 hours
  2. temperatureto cool
  3. customthe precipitated crystals were separated by filtration
  4. washwashed with water
  5. custompurified by silica gel column chromatography (eluted with chloroform)
  6. customThe product was recrystallized from ethanol

Sources & evidence

ORD record
ord-effd959f48cd4da9811c210bdd849ea1
Source dataset
uspto-grants-1987_12
Patent number
US04713457

Reaction notes

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