Water → HCID 68136538, compound

HRID 267765Notes

Reaction equation

HRID 267765 reaction equation
[CH3:1][C:2]([C:4]1[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:6][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:8][CH:9]=1)=O.[OH:22][CH:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[CH2:24][NH2:25].O>C1(C)C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[C:10]1([C:7]2[N:6]=[C:5]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:4]([CH2:2][CH:1]=[N:25][CH2:24][CH:23]([OH:22])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:9][N:8]=2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 1000PhenylethanolamineHCID 123183821-(2,4-Diphenylpyrimidin-5-yl)ethan-1-one

Product 1

HCID 68136538HCID 68136538, compoundYield 82.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 1140TolueneSolvent

Procedure

A mixture of 61.2 g (0.223 mole) of 2,4-diphenyl-5-pyrimidyl methyl ketone, 30.6 g (0.223 mole) of β-hydroxyphenethylamine and 3.0 g p-toluenesulfonic acid monohydrate in 750 ml toluene was stirred and refluxed using a Dean-Stark apparatus for 11.0 hours, amt. H2O evolved: 4:10 ml; theoretical amt.: 4.0 ml. The toluene was removed in vacuo and the residue was dissolved in 1000 ml chloroform. The solution was washed with 300 ml H2O, dried (MgSO4), and concentrated to dryness in vacuo. Recrystallization of the residue from ethanol gave in three crops 72 g (82%) of the product, m.p. 140°-144°.

Workup

  1. temperaturerefluxed
  2. customfor 11.0 hours
  3. customThe toluene was removed in vacuo
  4. dissolutionthe residue was dissolved in 1000 ml chloroform
  5. washThe solution was washed with 300 ml H2O
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to dryness in vacuo
  8. customRecrystallization of the residue from ethanol

Sources & evidence

ORD record
ord-57414204e5264f27b4985989239de9e1
Source dataset
uspto-grants-1976_03
Patent number
US03944581

Reaction notes

Loading…