Glycidol → HCID 13457951, compound

HRID 462676Notes

Reaction equation

HRID 462676 reaction equation
[CH2:1]1[O:3][CH:2]1[CH2:4][OH:5].[Br:6][C:7]1[CH:12]=[N:11][CH:10]([Cl:13])[N:9](Cl)[CH:8]=1.[H-].[Na+].[Cl-].[Na+].O.O>CN(C)C=O>[Br:6][C:7]1[C:8]([O:5][CH2:4][CH:2]2[CH2:1][O:3]2)=[N:9][C:10]([Cl:13])=[N:11][CH:12]=1

Participants

6

Reactant 4

HCID 11164GlycidolHCID 24758Sodium hydrideHCID 20397032HCID 20397032, compoundHCID 23713072Sodium chloride dihydrate

Product 1

HCID 13457951HCID 13457951, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of glycidol (13.0 g, 0.175 mole) and 5-bromo-2,3-dichloropyrimidine (40.0 g, 0.175 mole) in dimethylformamide (350 mL) was added dropwise to a stirring nitrogen-flushed, chilled suspension of sodium hydride (from 10.1 g, 0.21 mole, of NaH washed free of mineral oil) in dimethylformamide (350 mL). Following the addition, the reaction mixture was poured into 1:1 brine-water (4.5 l) and extracted with ethyl acetate (5×750 mL). Combined extracts were washed with water and brine, dried (MgSO4) and concentrated in vacuo to give 44.7 g of an oil which solidified. Trituration of the crude product in isopropyl alcohol-isopropyl ether gave 21.9 g (47%) of product, m.p. 63°-73°.

Workup

  1. customflushed
  2. temperaturechilled
  3. additionthe addition
  4. extractionextracted with ethyl acetate (5×750 mL)
  5. washCombined extracts were washed with water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93a2211395c74cd0a4c2ae7aa66c8165
Source dataset
uspto-grants-1985_05
Patent number
US04517188

Reaction notes

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