Sodium → HCID 88719423, compound

HRID 1262821Notes

Reaction equation

HRID 1262821 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][CH2:17][CH2:18][CH3:19])[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4].[Na:20]>C(O)C>[Na:20].[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][CH2:17][CH2:18][CH3:19])[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 20456185HCID 20456185, compound

Product 1

HCID 88719423HCID 88719423, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1,3-Di-n-butyl-6-thioxanthine (5,6 g) was treated with sodium (0,46 g) in absolute ethanol (20 ml) to give the 1,3-di-n-butyl-6-thioxanthine sodium salt by heating under reflux for one hour. 1-chloropropan-2-one (2,31 g) dissolved in ethanol (20 ml) was added dropwise and the reaction mixture heated under reflux for a further 5 hours. The reaction was then complete (as judged by TLC). After standing overnight, the precipitated sodium chloride was filtered off under suction. The dark filtrate was extracted with chloroform. The chloroform phase was washed three times with 1N NaOH, washed with water, dried with sodium sulphate, filtered and the chloroform was removed in vacuo to yield a dark brown residue. On crystallisation from ethanol the residue gave 1,3-di-n-butyl-7-(2-oxo-propyl)-6-thioxanthine as a white powder.

Sources & evidence

ORD record
ord-6ad1c240ab8c4d4caf7402423a3b9fae
Source dataset
uspto-grants-1984_06
Patent number
US04454138

Reaction notes

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