Methanesulfonyl chloride → HCID 70393229, compound

HRID 1723351Notes

Reaction equation

HRID 1723351 reaction equation
[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)[CH2:5][C@@H:4](O)[CH2:3]1.CS([Cl:23])(=O)=O>N1C=CC=CC=1>[CH3:1][N:2]1[C@H:16]2[C@@H:6]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]4[C:17]=3[C:14]([CH2:15]2)=[CH:13][NH:12]4)[CH2:5][C@@H:4]([Cl:23])[CH2:3]1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 15645931HCID 15645931, compound

Product 1

HCID 70393229HCID 70393229, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 5 g of 6-methyl-8β-hydroxyergoline in 80 ml of pyridine, 3.2 ml of methanesulfonyl chloride were slowly added at room temperature. The mixture obtained was heated at 80° C. for about 3 hours and then evaporated. The residue was taken up with chloroform and washed with saturated aqueous sodium bicarbonate solution and then water. Evaporation of the organic solvent yielded a residue which was chromatographed over a silica gel column using cyclohexane:acetone 8:2 by volume as eluant. Fractions containing the product were combined and crystallized from methanol to give 3.8 g of 6-methyl-8β-chloro-ergoline, m.p. 195°-197° C.

Workup

  1. customThe mixture obtained
  2. customevaporated
  3. washwashed with saturated aqueous sodium bicarbonate solution
  4. customEvaporation of the organic solvent
  5. customyielded a residue which
  6. customwas chromatographed over a silica gel column
  7. additionFractions containing the product
  8. customcrystallized from methanol

Sources & evidence

ORD record
ord-edba0dbd553c485d9dbd70339cb05693
Source dataset
uspto-grants-1989_08
Patent number
US04861793

Reaction notes

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