Imidazole → 1-(6-Methylergolin-8beta-ylmethyl)imidazole

HRID 986523Notes

Reaction equation

HRID 986523 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.CN(C)C=O.S(C1C=CC(C)=CC=1)(O[CH2:17][C@@H:18]1[CH2:32][C@H:31]2[C@@H:21]([CH2:22][C:23]3[C:33]4[C:26](=[CH:27][CH:28]=[CH:29][C:30]2=4)[NH:25][CH:24]=3)[N:20]([CH3:34])[CH2:19]1)(=O)=O>C(O)C>[CH3:34][N:20]1[C@H:21]2[C@@H:31]([C:30]3[CH:29]=[CH:28][CH:27]=[C:26]4[C:33]=3[C:23]([CH2:22]2)=[CH:24][NH:25]4)[CH2:32][C@@H:18]([CH2:17][N:3]2[CH:7]=[CH:6][N:5]=[CH:4]2)[CH2:19]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 139330156-Methylergolin-8beta-ylmethyl tosylate

Product 1

HCID 100637641-(6-Methylergolin-8beta-ylmethyl)imidazoleYield 58.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.0 g of 50% sodium hydride in an oil was added in small portions to a mixture of 2.0 g of imidazole and 20 ml of dimethylformamide, and the resulting mixture was stirred for 30 minutes. 3.0 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 filtered and washed with water. The crystals thus obtained were dissolved in ethanol, and the solution was concentrated to a volume of about 1/3, followed by allowing to cool to obtain 1.3 g of the titled compound as colorless prisms having a melting point of higher than 260° C. (with decomposition).

Workup

  1. temperaturewas then heated on a water bath for 3 hours
  2. temperatureto cool
  3. filtrationthe precipitated crystals were filtered
  4. washwashed with water
  5. customThe crystals thus obtained
  6. concentrationthe solution was concentrated to a volume of about 1/3
  7. temperatureto cool

Sources & evidence

ORD record
ord-c12106e00eed45cba9a84785d133a144
Source dataset
uspto-grants-1987_12
Patent number
US04713457

Reaction notes

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