Water → HCID 13295058, compound

HRID 1462350Notes

Reaction equation

HRID 1462350 reaction equation
[C:1]([NH:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][OH:15])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H-].[Na+].Cl[C:21]1[N:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=1.O>CS(C)=O>[C:1]([NH:4][C:5]1[CH:17]=[CH:16][C:8]([O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][C:21]2[N:26]=[CH:25][C:24]([Cl:27])=[CH:23][N:22]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5906412,5-DichloropyrimidineHCID 13295056HCID 13295056, compound

Product 1

HCID 13295058HCID 13295058, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2-[2-(4-Acetamidophenoxy)ethoxy]ethanol (9 g) was dissolved in dry dimethylsulfoxide (60 ml) and granular sodium hydride (0.9 g) was added portionwise to the solution. 2,5-Dichloropyrimidine (5.6 g) was slowly added to the cooled stirred solution and on completion of the addition the mixture was stirred at room temperature for 1 hour. The mixture was poured into water (200 ml) and the solid was collected by filtration. The product was recrystallised from ethanol/water to give 2-{2-[2(4-acetamidophenoxy)ethoxy]ethoxy}-5-chloropyrimidine (8.4 g), m.p. 110° C.

Workup

  1. additionon completion of the addition the mixture
  2. stirringwas stirred at room temperature for 1 hour
  3. filtrationthe solid was collected by filtration
  4. customThe product was recrystallised from ethanol/water

Sources & evidence

ORD record
ord-3244ddef9a884e4289dd2768bebe0161
Source dataset
uspto-grants-1984_07
Patent number
US04460588

Reaction notes

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