Hydrochloric Acid → HCID 19820461, compound

HRID 1030499Notes

Reaction equation

HRID 1030499 reaction equation
I.[CH3:2][N:3]1[CH2:8][CH2:7][CH2:6][N:5]=[C:4]1SC.[C:11]1([CH:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:18][NH2:19])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[ClH:26]>CO.[OH-].[Na+].C(Cl)Cl>[ClH:26].[C:20]1([CH:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:18][NH:19][C:4]2[N:3]([CH3:2])[CH2:8][CH2:7][CH2:6][N:5]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 775752,2-DiphenylethylamineHCID 12397474HCID 12397474, compound

Product 1

HCID 19820461HCID 19820461, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Conditions

Temperature
0 °C

Procedure

A flask containing 1-methyl-2-methylthio-1,4,5,6-tetrahydropyrimidine hydroiodide (9.80 g, 3.60×10-2 mole) and 2,2-diphenylethylamine (7.49 g, 3.80×10-2 mole) was immersed in an oil bath which had been preheated to ca. 155° C. The reaction was stirred at between 150°-170° C. for 45 minutes. The resulting yellow glass was dissolved in methanol. Most of the methanol was evaporated at reduced pressure and isopropanol was added. The evaporation was continued, being stopped periodically for the addition of small portions of isopropanol. A solid forms which was collected by filtration affording a colorless solid. This was dissolved in a two phase mixture of 50% aqueous NaOH (60 ml) and CH2Cl2 (100 ml). After stirring overnight, the CH2Cl2 layer was separated. The aqueous alkaline layer was extracted with CH2Cl2 (2×). The CH2Cl2 layers were combined, washed with H2O (2×), washed with saturated aqueous NaCl, and dried over anhydrous Na2SO4. The drying agent was removed by filtration and the filtrate was evaporated at reduced pressure leaving a foam which was dissolved in methanol (40 ml). This solution was cooled to 0° C. before being treated with a methanolic solution of HCl. The methanol was partially evaporated and isopropanol was added. The evaporation was continued, being stopped periodically for the addition of small portions of isopropanol. A solid formed and the flask was placed in the refrigerator. After several hours, the product was collected by filtration. Crystallization from isopropanol afforded 2-(2,2-diphenylethylamino)-1-methyl-1,4,5,6-tetrahydropyrimidine hydrochloride as a colorless solid: 2.66 g (22%), m.p. 155°-157° C.

Workup

  1. customwas immersed in an oil bath
  2. customhad been preheated to ca. 155° C
  3. customMost of the methanol was evaporated at reduced pressure and isopropanol
  4. additionwas added
  5. customThe evaporation
  6. additionbeing stopped periodically for the addition of small portions of isopropanol
  7. filtrationA solid forms which was collected by filtration
  8. customaffording a colorless solid
  9. stirringAfter stirring overnight
  10. customthe CH2Cl2 layer was separated
  11. extractionThe aqueous alkaline layer was extracted with CH2Cl2 (2×)
  12. washwashed with H2O (2×)
  13. washwashed with saturated aqueous NaCl
  14. dry with materialdried over anhydrous Na2SO4
  15. customThe drying agent was removed by filtration
  16. customthe filtrate was evaporated at reduced pressure
  17. customleaving a foam which
  18. customThe methanol was partially evaporated
  19. additionisopropanol was added
  20. customThe evaporation
  21. additionbeing stopped periodically for the addition of small portions of isopropanol
  22. customA solid formed
  23. waitAfter several hours
  24. filtrationthe product was collected by filtration
  25. customCrystallization from isopropanol

Sources & evidence

ORD record
ord-c4cfaff85d9649e7a6bcec0df2b4a543
Source dataset
uspto-grants-1992_04
Patent number
US05106845

Reaction notes

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