Sodium hydride → HCID 10065497, compound

HRID 986532Notes

Reaction equation

HRID 986532 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[NH:6][CH:7]=[CH:8][N:9]=1)[CH3:4].S(C1C=CC(C)=CC=1)(O[CH2:14][C@@H:15]1[CH2:29][C@H:28]2[C@@H:18]([CH2:19][C:20]3[C:30]4[C:23](=[CH:24][CH:25]=[CH:26][C:27]2=4)[NH:22][CH:21]=3)[N:17]([CH3:31])[CH2:16]1)(=O)=O>CN(C)C=O>[CH2:3]([C:5]1[N:6]([CH2:14][C@@H:15]2[CH2:29][C@H:28]3[C@@H:18]([CH2:19][C:20]4[C:30]5[C:23](=[CH:24][CH:25]=[CH:26][C:27]3=5)[NH:22][CH:21]=4)[N:17]([CH3:31])[CH2:16]2)[CH:7]=[CH:8][N:9]=1)[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 661302-EthylimidazoleHCID 139330156-Methylergolin-8beta-ylmethyl tosylate

Product 1

HCID 10065497HCID 10065497, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.9 g of 50% sodium hydride in an oil was added in small portions to a mixture of 3.0 g of 2-ethylimidazole and 60 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 1.5 hours. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluted with acetone). The product was recrystallized from methanolisopropyl alcohol to obtain 1.5 g of the titled compound having a melting point of 232°-237° C.

Workup

  1. temperaturewas then heated on a water bath for 1.5 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (eluted with acetone)
  4. customThe product was recrystallized from methanolisopropyl alcohol

Sources & evidence

ORD record
ord-340c671d331a44bfa8fcd96b92fa2bc1
Source dataset
uspto-grants-1987_12
Patent number
US04713457

Reaction notes

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