Dimethylformamide → 1-(6-Methylergolin-8beta-ylmethyl)-1,2,4-triazole

HRID 986528Notes

Reaction equation

HRID 986528 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[N:6][CH:5]=[N: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>O>[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]=[N:6][CH:5]=[N:4]2)[CH2:19]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 92571H-1,2,4-TriazoleHCID 24758Sodium hydrideHCID 139330156-Methylergolin-8beta-ylmethyl tosylate

Product 1

HCID 98885351-(6-Methylergolin-8beta-ylmethyl)-1,2,4-triazoleYield 53.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.4 g of 50% sodium hydride in an oil was added in small portions to a mixture of 2.0 g of 1,2,4-triazole and 20 ml of dimethylformamide, and the resulting mixture was stirred for 30 minutes. 2.0 g of 6-methylergolin-8β-ylmethyl tosylate was added to the mixture which was then heated on a water bath for 1 hour. After allowing the mixture to cool, water was added to the reaction mixture, and the precipitated crystals were separated by filtration, washed with water and purified by alumina column chromatography (eluted with dichloromethane). The product was recrystallized from methanol to obtain 0.8 g of the titled compound as colorless needles having a melting point of 245°-253° C.

Workup

  1. temperaturewas then heated on a water bath for 1 hour
  2. temperatureto cool
  3. customthe precipitated crystals were separated by filtration
  4. washwashed with water
  5. custompurified by alumina column chromatography (eluted with dichloromethane)
  6. customThe product was recrystallized from methanol

Sources & evidence

ORD record
ord-d6f5eb6e92eb44df8d9baf2b6f9cc0cc
Source dataset
uspto-grants-1987_12
Patent number
US04713457

Reaction notes

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