Sodium hydride → 1-(6-Methylergolin-8beta-ylmethyl)tetrazole

HRID 986529Notes

Reaction equation

HRID 986529 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][N:5]=[N:4]1.S(C1C=CC(C)=CC=1)(O[CH2:12][C@@H:13]1[CH2:27][C@H:26]2[C@@H:16]([CH2:17][C:18]3[C:28]4[C:21](=[CH:22][CH:23]=[CH:24][C:25]2=4)[NH:20][CH:19]=3)[N:15]([CH3:29])[CH2:14]1)(=O)=O>CN(C)C=O>[CH3:29][N:15]1[C@H:16]2[C@@H:26]([C:25]3[CH:24]=[CH:23][CH:22]=[C:21]4[C:28]=3[C:18]([CH2:17]2)=[CH:19][NH:20]4)[CH2:27][C@@H:13]([CH2:12][N:3]2[CH:7]=[N:6][N:5]=[N:4]2)[CH2:14]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 139330156-Methylergolin-8beta-ylmethyl tosylateHCID 178418441HCID 178418441, compound

Product 1

HCID 100409401-(6-Methylergolin-8beta-ylmethyl)tetrazoleYield 31.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.7 g of 50% sodium hydride in an oil was added in small portions to a mixture of 5.1 g of tetrazole and 30 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 11 hours. The solvent was distilled off under reduced pressure, and the residue was purified by alumina column chromatography (eluted with acetone). The product was recrystallized from acetone to obtain 0.7 g of the titled compound as colorless needles having a melting point of 206°-209° C.

Workup

  1. temperaturewas then heated on a water bath for 11 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe residue was purified by alumina column chromatography (eluted with acetone)
  4. customThe product was recrystallized from acetone

Sources & evidence

ORD record
ord-9a29efd8a44a41c994139f5995a3a73f
Source dataset
uspto-grants-1987_12
Patent number
US04713457

Reaction notes

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