Toluene → S-[(6-Chloro-5-oxo-5H-thiazolo[3,2-a]pyrimidin-7-yl)methyl] O,O-dimethyl phosphorodithioate

HRID 1075294Notes

Reaction equation

HRID 1075294 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[N:6]2[CH:9]=[CH:10][S:11][C:5]2=[N:4][C:3]=1[CH2:12]Cl.C1(C)C=CC=CC=1.[P:21]([S-:27])(=[S:26])([O:24][CH3:25])[O:22][CH3:23].[NH4+]>CO>[P:21]([S:27][CH2:12][C:3]1[N:4]=[C:5]2[S:11][CH:10]=[CH:9][N:6]2[C:7](=[O:8])[C:2]=1[Cl:1])(=[S:26])([O:24][CH3:25])[O:22][CH3:23]

Participants

5

Reactant 3

HCID 1140TolueneHCID 6451175Ammonium O,O-dimethyl dithiophosphateHCID 132329226-Chloro-7-(chloromethyl)-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Product 1

HCID 13232940S-[(6-Chloro-5-oxo-5H-thiazolo[3,2-a]pyrimidin-7-yl)methyl] O,O-dimethyl phosphorodithioate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound of EXAMPLE 2 (7 g) and 100 ml of toluene was stirred and heated to 70°. To this mixture was added, dropwise, a solution of 14 g ammonium dimethyl phosphorodithioate in 200 ml methanol. The resulting mixture was kept at 70° for 6 hours, then the methanol was distilled off. Toluene (400 ml) was added, and the mixture was washed with water, separated, dried and evaporated under reduced pressure. The solid which remained was washed with toluene and filtered. The solid, m.p. 125°-130°, weighed 2.5 g.

Workup

  1. temperatureheated to 70°
  2. additionTo this mixture was added
  3. distillationthe methanol was distilled off
  4. additionToluene (400 ml) was added
  5. washthe mixture was washed with water
  6. customseparated
  7. customdried
  8. customevaporated under reduced pressure
  9. washThe solid which remained was washed with toluene
  10. filtrationfiltered

Sources & evidence

ORD record
ord-40ccea17e8c74c6ab6bb42fa09a6de52
Source dataset
uspto-grants-1983_07
Patent number
US04395551

Reaction notes

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