Sodium Hydroxide → HCID 12050165, compound

HRID 2305388Notes

Reaction equation

HRID 2305388 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:15]3[N:14]=[C:13]([CH:16]([CH3:18])[CH3:17])[NH:12][C:11]=3[C:10](=O)[NH:9][C:8]2=[O:20])=[CH:4][CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:24].[OH-].[Na+]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][N:7]2[C:15]3[N:14]=[C:13]([CH:16]([CH3:18])[CH3:17])[NH:12][C:11]=3[C:10](=[S:24])[NH:9][C:8]2=[O:20])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 18432847HCID 18432847, compound

Product 1

HCID 12050165HCID 12050165, compoundYield 135.5%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6212ChloroformSolvent

Conditions

Temperature
-5 °C

Procedure

12.75 g of 3-(4-chlorobenzyl)-8-isopropyl-xanthine and 10.67 g of phosphorus pentasulfide were heated under reflux in 200 ml of pyridine for 5.5 hours. After cooling to −5° C., 52.5 ml of 2N NaOH was added over 15 minutes. The solid was filtered off and the filtrate evaporated in vacuo to dryness. The residue was suspended in 250 ml of water (pH 7), the solid collected and washed. The crude product was redissolved in 200 ml of 2N NaOH, treated with 1.4 g of charcoal, filtered and neutralized with 38 ml of 5N HCl to pH 7. The solid was collected, washed and dried to give the crude title compound (12.36 g). This was dissolved in chloroform and filtered through 60 g of silica gel, thereby affording the title compound (10.89 g) as an off-white solid mp 235-6° C. (from acetone).

Workup

  1. filtrationThe solid was filtered off
  2. customthe filtrate evaporated in vacuo to dryness
  3. customthe solid collected
  4. washwashed
  5. dissolutionThe crude product was redissolved in 200 ml of 2N NaOH
  6. additiontreated with 1.4 g of charcoal
  7. filtrationfiltered
  8. customThe solid was collected
  9. washwashed
  10. customdried
  11. customto give the crude title compound (12.36 g)
  12. filtrationfiltered through 60 g of silica gel

Sources & evidence

ORD record
ord-f8eb35bae81f463cb5f047af95b5aebe
Source dataset
uspto-grants-2002_08
Patent number
US06440979B1

Reaction notes

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