Thionyl Chloride → HCID 53934989, compound

HRID 1814987Notes

Reaction equation

HRID 1814987 reaction equation
C([O:4][C@H:5]([CH3:25])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[C:16]([CH2:22]O)=[N:15][C:14]=2[N:13]([CH3:24])[C:11]1=[O:12])(=O)C.S(Cl)([Cl:28])=O>>[OH:4][C@H:5]([CH3:25])[CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[C:19](=[O:20])[C:18]2[N:17]([CH3:21])[C:16]([CH2:22][Cl:28])=[N:15][C:14]=2[N:13]([CH3:24])[C:11]1=[O:12]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 54327557HCID 54327557, compound

Product 1

HCID 53934989HCID 53934989, compoundYield 96%

Procedure

To thionyl chloride (30 ml) stirred at 0-5° C. was added (R)-1-(5-acetoxyhexyl)-8-hydroxymethyl-3,7-dimethylxanthine (6.3 g, 17.9 mmol). After stirring overnight at room temperature, unreacted thionyl chloride and volatile byproducts were evaporated under reduced pressure. To the residual oil was added methanol (300 ml) followed by hydrogen chloride in ether (1.0 M, 20 ml). After stirring for 12 hours, volatile materials were evaporated under reduced pressure to provide (R)-1-(5-hydroxyhexyl)-8-chloromethyl-3,7-dimethylxanthine (5.6 g, 96% yield) as a white solid.

Workup

  1. customunreacted thionyl chloride and volatile byproducts were evaporated under reduced pressure
  2. additionTo the residual oil was added methanol (300 ml)
  3. stirringAfter stirring for 12 hours
  4. customvolatile materials were evaporated under reduced pressure

Sources & evidence

ORD record
ord-68d49a75eb0c40a180fb2dd0ce5a758d
Source dataset
uspto-grants-2005_04
Patent number
US06878715B1

Reaction notes

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