Sodium hydride → HCID 13295057, compound

HRID 1462349Notes

Reaction equation

HRID 1462349 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([O:9][CH2:10][CH2:11][OH:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[H-].[Na+].Cl[C:18]1[N:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=1>O1CCCC1>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:8]([O:9][CH2:10][CH2:11][O:12][C:18]2[N:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 170834Acetamide, N-[4-(2-hydroxyethoxy)phenyl]-HCID 5906412,5-Dichloropyrimidine

Product 1

HCID 13295057HCID 13295057, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-(4-acetamidophenoxy)ethanol (25 g), granular sodium hydride (3.1 g) and dry tetrahydrofuran (250 ml) was heated under reflux for a period of 2 hours. 2,5-Dichloropyrimidine* (19 g) was added and the mixture was heated under reflux for a further 8 hours. The solvent was removed by distillation under reduced pressure, water was added and the crystalline product was collected and dried to give 2-[2-(4-acetamidophenoxy)ethoxy]-5-chloropyrimidine (35 g), m.p. 160° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for a period of 2 hours
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for a further 8 hours
  5. customThe solvent was removed by distillation under reduced pressure, water
  6. additionwas added
  7. customthe crystalline product was collected
  8. customdried

Sources & evidence

ORD record
ord-44f7473e20a8418da670f967433871d2
Source dataset
uspto-grants-1984_07
Patent number
US04460588

Reaction notes

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