4-Toluenesulfonyl chloride → HCID 88726054, compound

HRID 1112778Notes

Reaction equation

HRID 1112778 reaction equation
[CH3:1][O:2][C@:3]12[CH2:17][C@@H:16]([CH2:18][OH:19])[CH2:15][N:14]([CH3:20])[C@@H:13]1[CH2:12][C:11]1[C:21]3[C:8]([N:9]([CH3:22])[CH:10]=1)=[CH:7][CH:6]=[CH:5][C:4]2=3.C(N(CC)CC)C.[S:30](Cl)([C:33]1[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=1)(=[O:32])=[O:31]>C(Cl)Cl>[S:30]([O:19][CH2:18][C@@H:16]1[CH2:17][C@@:3]2([O:2][CH3:1])[C@@H:13]([CH2:12][C:11]3[C:21]4[C:8](=[CH:7][CH:6]=[CH:5][C:4]2=4)[N:9]([CH3:22])[CH:10]=3)[N:14]([CH3:20])[CH2:15]1)([C:33]1[CH:39]=[CH:38][C:36]([CH3:37])=[CH:35][CH:34]=1)(=[O:32])=[O:31]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 9796365(10-Methoxy-1,6-dimethylergolin-8beta-yl)methanol

Product 1

HCID 88726054HCID 88726054, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 10 g of 10-methoxy-1,6-dimethylergoline-8β-methanol, 12.4 ml of triethylamine, and 12.6 g of tosyl chloride in 200 ml of methylene chloride is refluxed 5 hr. The solution is washed first with 10% Na2CO3 and then with water, the solvent is evaporated in vacuo, and the residue is crystallized from methanol to give 11 g of 10-methoxy-1,6-dimethylergoline-8β-methanol tosylate; m.p. 169° C.

Workup

  1. temperatureis refluxed 5 hr
  2. washThe solution is washed first with 10% Na2CO3
  3. customwith water, the solvent is evaporated in vacuo
  4. customthe residue is crystallized from methanol

Sources & evidence

ORD record
ord-efe6e5a450324c3e8107528b0c513bbb
Source dataset
uspto-grants-1978_10
Patent number
US04123613

Reaction notes

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