Sodium hydride → HCID 10453132, compound

HRID 986537Notes

Reaction equation

HRID 986537 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:5]=[CH:6][NH:7][C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10].S(C1C=CC(C)=CC=1)(O[CH2:18][C@@H:19]1[CH2:33][C@H:32]2[C@@H:22]([CH2:23][C:24]3[C:34]4[C:27](=[CH:28][CH:29]=[CH:30][C:31]2=4)[NH:26][CH:25]=3)[N:21]([CH3:35])[CH2:20]1)(=O)=O>CN(C)C=O>[CH3:3][C:4]1[N:5]=[CH:6][N:7]([CH2:18][C@@H:19]2[CH2:33][C@H:32]3[C@@H:22]([CH2:23][C:24]4[C:34]5[C:27](=[CH:28][CH:29]=[CH:30][C:31]3=5)[NH:26][CH:25]=4)[N:21]([CH3:35])[CH2:20]2)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 139330156-Methylergolin-8beta-ylmethyl tosylateHCID 178470400HCID 178470400, compound

Product 1

HCID 10453132HCID 10453132, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.6 g of 50% sodium hydride in an oil was added in small portions to a mixture of 10 g of ethyl 4-methyl-5-imidazolecarboxylate and 70 ml of dimethylformamide, and the resulting mixture was stirred for 30 minutes. 4.1 g of 6-methylergolin-8β-ylmethyl tosylate was added to the mixture which was then heated on a water bath for 2 hours. The solvent was distilled off under reduced pressure, and the residue was subjected to alumina column chromatography eluting with ethyl acetate to obtain ethyl 4-methyl-1-(6-methylergolin-8β-ylmethyl)-5-imidazolecarboxylate from the first fraction. The product was recrystallized from dichloromethane-diethyl ether and was colorless prisms having a melting point of 225°-227° C. Yield, 0.7 g. This compound is hereinafter referred to as Compound 15A.

Workup

  1. temperaturewas then heated on a water bath for 2 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-30873a5c850d4a899411784e777a64a0
Source dataset
uspto-grants-1987_12
Patent number
US04713457

Reaction notes

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