Ethanol → HCID 178525523, compound

HRID 1090239Notes

Reaction equation

HRID 1090239 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][CH2:9][NH2:10].I.CS[C:14]1[C:22]2[CH:23]=[CH:24][CH:25]=[C:20]3[C:21]=2[C:16](=[CH:17][CH:18]=[CH:19]3)[N:15]=1.C(O)C.[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33]>CC(C)=O>[C:29]([OH:36])(=[O:35])/[CH:30]=[CH:31]/[C:32]([OH:34])=[O:33].[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][CH2:8][CH2:9][NH:10][C:14]1[C:22]2[CH:23]=[CH:24][CH:25]=[C:20]3[C:21]=2[C:16](=[CH:17][CH:18]=[CH:19]3)[N:15]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 968902-(2-Aminoethoxy)pyridineHCID 444972Fumaric AcidHCID 201506502-Methylthiobenz(cd)indole hydriodide

Product 1

HCID 178525523HCID 178525523, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture consisting of 3.0 grams of 2-(2-pyridinyloxy) ethylamine, 6.5 grams of 2-methylthiobenz(cd)indole hydriodide, and 150 ml of ethanol was stirred and heated under reflux, utilizing the conditions of Example 16. The crude free base (weight, 7.1 grams) was dissolved in 20 ml of acetone and added to a stirred boiling solution of 5.5 grams of fumaric acid in 1200 ml of acetone. After cooling the precipitate of the title compound was collected, washed with acetone, and dried; yield, 7.6 grams; mp 184° C.-185° C. with decomposition.

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. additionadded to a stirred

Sources & evidence

ORD record
ord-946965078e15461fb924080b3ca468db
Source dataset
uspto-grants-1992_01
Patent number
US05081131

Reaction notes

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