Thionyl Chloride → 8-alpha-Chloroethylcaffeine

HRID 1283378Notes

Reaction equation

HRID 1283378 reaction equation
O[CH:2]([C:4]1[N:13]([CH3:14])[C:12]2[C:11](=[O:15])[N:9]([CH3:10])[C:8](=[O:16])[N:7]([CH3:17])[C:6]=2[N:5]=1)[CH3:3].S(Cl)([Cl:20])=O>>[Cl:20][CH:2]([C:4]1[N:13]([CH3:14])[C:12]2[C:11](=[O:15])[N:9]([CH3:10])[C:8](=[O:16])[N:7]([CH3:17])[C:6]=2[N:5]=1)[CH3:3]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2352888-(1-Hydroxyethyl)-1,3,7-trimethyl-3,7-dihydro-1h-purine-2,6-dione

Product 1

HCID 681383658-alpha-Chloroethylcaffeine

Procedure

10 g of 8-α-hydroxyethylcaffeine (Arch. der Pharmazie, 289, 453, 1956) are added and under shaking with 100 ml of thionyl chloride. After 6 hours of reflux, the excess of reagent is evaporated to dryness under reduced pressure and the solid residue washed with petroleum ether. Nearly pure 8-α-chloroethylcaffeine is obtained with a quantitative yield, melting at 190° C from anhydrous benzene.

Workup

  1. temperatureAfter 6 hours of reflux
  2. customthe excess of reagent is evaporated to dryness under reduced pressure
  3. washthe solid residue washed with petroleum ether

Sources & evidence

ORD record
ord-0c26de3d77094437ac04c49e2678556c
Source dataset
uspto-grants-1976_08
Patent number
US03975389

Reaction notes

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