Water → HCID 14014538, compound

HRID 620145Notes

Reaction equation

HRID 620145 reaction equation
[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([CH2:14][CH3:15])[NH:10][C:9]=2[C:8](=O)[NH:7][C:6]1=[O:17])[CH2:2][CH2:3][CH3:4].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:19].O>N1C=CC=CC=1>[CH2:1]([N:5]1[C:13]2[N:12]=[C:11]([CH2:14][CH3:15])[NH:10][C:9]=2[C:8](=[S:19])[NH:7][C:6]1=[O:17])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 14817Phosphorus sulfide (P2S5)HCID 14014537HCID 14014537, compound

Product 1

HCID 14014538HCID 14014538, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

11.8 g (50 mM.) of 3-butyl-8-ethyl-xanthine (mp 304°-9° C., and 18.2 g (82 nM.) of phosphorus pentasulfide were refluxed in 170 ml of pyridine for 2 hrs. The solution was cooled to ambient temperature and treated slowly with 110 ml. of water (exothermic). The suspension was concentrated to 100 ml. in vacuo at 60° C., further diluted with 140 ml. of water, and concentrated again to about 120 ml. The crude product was collected and washed with ice water. The dried material (11.1 g.) was dissolved in about 100 ml. of chloroform, and the solution filtered through 55 g. of silicagel. The chloroform was evaporated and the residue crystallized from acetone-ether: 7.2 g. (57.5%) of 3-butyl-8-ethyl-6-thioxanthine, mp. 206°-7° C. From the mother liquor, a second crop of 2.1 g. (16.3%) was obtained.

Workup

  1. additiontreated slowly with 110 ml
  2. concentrationThe suspension was concentrated to 100 ml
  3. additionin vacuo at 60° C., further diluted with 140 ml
  4. concentrationof water, and concentrated again to about 120 ml
  5. customThe crude product was collected
  6. washwashed with ice water
  7. dissolutionThe dried material (11.1 g.) was dissolved in about 100 ml
  8. filtrationof chloroform, and the solution filtered through 55 g
  9. customThe chloroform was evaporated
  10. customthe residue crystallized from acetone-ether
  11. custom(16.3%) was obtained

Sources & evidence

ORD record
ord-9837bf97f0814d7db5ea8113dfd73a61
Source dataset
uspto-grants-1989_04
Patent number
US04820709

Reaction notes

Loading…