2-Bromoethanol → HCID 12534514, compound

HRID 1075172Notes

Reaction equation

HRID 1075172 reaction equation
[CH2:1](Br)[CH2:2][OH:3].[K].[CH3:6][S:7][C:8]1[C:13]([F:14])=[CH:12][NH:11][C:10](=[O:15])[N:9]=1>CN(C)C=O>[OH:3][CH2:2][CH2:1][N:11]1[CH:12]=[C:13]([F:14])[C:8]([S:7][CH3:6])=[N:9][C:10]1=[O:15]

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 5462222PotassiumHCID 178503576HCID 178503576, compound

Product 1

HCID 12534514HCID 12534514, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethylene bromohydrin (0.023 mol) was added to a solution of the potassium salt of 4-methylthio-5-fluoropyrimid-2-one (0.015 mol) in dimethylformamide (65 ml) and the reaction mixture was stirred at room temperature for 24 h before evaporation at reduced pressure (1 mm Hg). The residue was extracted with chloroform, the solution was washed with aqueous 2 N NaOH, with water and was dried (MgSO4) before evaporation. The solid residue was recrystallized from acetone; yield 77%, m.p. 161°-162° C. (Found: C, 41.36; H, 4.62. Calc. for C7H9FN2O2S: C, 41.17; H, 4.44).

Workup

  1. extractionThe residue was extracted with chloroform
  2. washthe solution was washed with aqueous 2 N NaOH, with water
  3. dry with materialwas dried (MgSO4)
  4. custombefore evaporation
  5. customThe solid residue was recrystallized from acetone

Sources & evidence

ORD record
ord-5fa402a8163840709409ad6290372f80
Source dataset
uspto-grants-1983_07
Patent number
US04395406

Reaction notes

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