Sodium hydride → HCID 10043370, compound

HRID 986536Notes

Reaction equation

HRID 986536 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[NH:6][CH:7]=[C:8]([CH3:10])[N:9]=1)[CH3:4].S(C1C=CC(C)=CC=1)(O[CH2:15][C@@H:16]1[CH2:30][C@H:29]2[C@@H:19]([CH2:20][C:21]3[C:31]4[C:24](=[CH:25][CH:26]=[CH:27][C:28]2=4)[NH:23][CH:22]=3)[N:18]([CH3:32])[CH2:17]1)(=O)=O>CN(C)C=O>[CH2:3]([C:5]1[N:6]([CH2:15][C@@H:16]2[CH2:30][C@H:29]3[C@@H:19]([CH2:20][C:21]4[C:31]5[C:24](=[CH:25][CH:26]=[CH:27][C:28]3=5)[NH:23][CH:22]=4)[N:18]([CH3:32])[CH2:17]2)[CH:7]=[C:8]([CH3:10])[N:9]=1)[CH3:4]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 139330156-Methylergolin-8beta-ylmethyl tosylateHCID 178437635HCID 178437635, compound

Product 1

HCID 10043370HCID 10043370, compoundYield 28.7%

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 9.0 g of 2-ethyl-4-methylimidazole 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 water was added to the resulting residue. The precipitated crystals were separated by filtration, washed with water and recrystallized from methanol to obtain 1.0 g of the titled compound as colorless needles having a melting point of 172°-174° C.

Workup

  1. temperaturewas then heated on a water bath for 2 hours
  2. distillationThe solvent was distilled off under reduced pressure, and water
  3. additionwas added to the resulting residue
  4. customThe precipitated crystals were separated by filtration
  5. washwashed with water
  6. customrecrystallized from methanol

Sources & evidence

ORD record
ord-9b54d25c1d3c4559bdb5f1e79ae130b4
Source dataset
uspto-grants-1987_12
Patent number
US04713457

Reaction notes

Loading…