Hydrochloric Acid → 1,3-Di-n-butyl-8-chloro Xanthine

HRID 3633Notes

Reaction equation

HRID 3633 reaction equation
[CH2:1]([N:5]1[C:14](=[O:15])[C:13]2[NH:12][C:11]([N+]([O-])=O)=[N:10][C:9]=2[N:8]([CH2:19][CH2:20][CH2:21][CH3:22])[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4].[ClH:23]>>[CH2:1]([N:5]1[C:14](=[O:15])[C:13]2[NH:12][C:11]([Cl:23])=[N:10][C:9]=2[N:8]([CH2:19][CH2:20][CH2:21][CH3:22])[C:6]1=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 99444751,3-Di-n-butyl-8-nitro Xanthine

Product 1

HCID 99660571,3-Di-n-butyl-8-chloro Xanthine

Procedure

1,3-Di-n-butyl-8-nitro xanthine (0.5 g, 0.0016 mol) was refluxed for 18 hours with concentrated hydrochloric acid (8 ml). The reaction mixture was extracted with dichloromethane (20 ml), the organic layer washed with water to neutrality and then dried over anhydrous sodium sulphate. The solvent was then removed by evaporation in vacuo and the residue was recrystallised from ethanol, to give the title compound, yield 0.38 g (73%), m.pt. 152° C.

Workup

  1. extractionThe reaction mixture was extracted with dichloromethane (20 ml)
  2. washthe organic layer washed with water to neutrality
  3. dry with materialdried over anhydrous sodium sulphate
  4. customThe solvent was then removed by evaporation in vacuo
  5. customthe residue was recrystallised from ethanol

Sources & evidence

ORD record
ord-15f8af76545c4427afa00c3550df7223
Source dataset
uspto-grants-1998_03
Patent number
US05734051

Reaction notes

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