Methane → HCID 10249339, compound

HRID 986535Notes

Reaction equation

HRID 986535 reaction equation
[H-].[Na+].[C:3]1([C:9]2[NH:10][CH:11]=[CH:12][N:13]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.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.C>ClCCl.CN(C)C=O>[CH3:35][N:21]1[C@H:22]2[C@@H:32]([C:31]3[CH:30]=[CH:29][CH:28]=[C:27]4[C:34]=3[C:24]([CH2:23]2)=[CH:25][NH:26]4)[CH2:33][C@@H:19]([CH2:18][N:13]2[CH:12]=[CH:11][N:10]=[C:9]2[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:20]1

Participants

7

Reactant 4

HCID 297MethaneHCID 24758Sodium hydrideHCID 695912-PhenylimidazoleHCID 139330156-Methylergolin-8beta-ylmethyl tosylate

Product 1

HCID 10249339HCID 10249339, compoundYield 30.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

1.0 g of 50% sodium hydride in an oil was added in small portions to a mixture of 10.5 g of 2-phenylimidazole and 60 ml of dimethylformamide, and the resulting mixture was stirred for 30 minutes. 3.5 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 purified by silica gel column chromatography (eluted with acetone). The product thus obtained was treated with charcoal in dichloromethane, and recrystallized from dichloromethaneisopropyl acetate to obtain 1.0 g of the titled compound as colorless prisms having a melting point of 193°-195° C.

Workup

  1. temperaturewas then heated on a water bath for 2 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 thus obtained
  5. customrecrystallized from dichloromethaneisopropyl acetate

Sources & evidence

ORD record
ord-b08cd8e6ec004ccba75db8c32b913723
Source dataset
uspto-grants-1987_12
Patent number
US04713457

Reaction notes

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