Potassium Carbonate → HCID 20456187, compound

HRID 1262819Notes

Reaction equation

HRID 1262819 reaction equation
[CH2:1]([N:5]1[C:14](=[S:15])[C:13]2[NH:12][CH:11]=[N:10][C:9]=2[N:8]([CH2:16][CH3:17])[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26](=[O:28])[CH3:27]>CN(C)C=O>[CH2:1]([N:5]1[C:14](=[S:15])[C:13]2[N:12]([CH2:25][C:26](=[O:28])[CH3:27])[CH:11]=[N:10][C:9]=2[N:8]([CH2:16][CH3:17])[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11715BromoacetoneHCID 20456180HCID 20456180, compound

Product 1

HCID 20456187HCID 20456187, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

1-n-Butyl-3-ethyl-6-thioxanthine (4 g) was dissolved in dimethyl formamide (30 ml) and a small amount of potassium carbonate was added. To this mixture, 1-bromopropan-2-one (2,7 g) was added dropwise at room temperature, with stirring. The reaction was heated at about 50° C. for two hours. The reaction mixture was then extracted with chloroform several times, the chloroform phase washed with 1N KOH and water, dried with sodium sulphate, filtered and the chloroform removed in vacuo to yield a red/brown oil which, on crystallisation in a mixture of ethylacetate/petroleum, gave 1-n-butyl-3-ethyl-7-(2-oxopropyl)-6-thioxanthine as a white powder.

Workup

  1. extractionThe reaction mixture was then extracted with chloroform several times
  2. washthe chloroform phase washed with 1N KOH and water
  3. dry with materialdried with sodium sulphate
  4. filtrationfiltered
  5. customthe chloroform removed in vacuo
  6. customto yield a red/brown oil which
  7. customon crystallisation
  8. additionin a mixture of ethylacetate/petroleum

Sources & evidence

ORD record
ord-ddb33db3846b4602ad2964597ce376f9
Source dataset
uspto-grants-1984_06
Patent number
US04454138

Reaction notes

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