Potassium Carbonate → 8-methyl-3,4-dihydro-2H-[1,3]thiazino[3,2-a]benzimidazole

HRID 1926492Notes

Reaction equation

HRID 1926492 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:5]=2[N:6]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:19][CH2:20][CH2:21]I>CN(C)C=O>[CH3:11][C:9]1[CH:8]=[CH:7][C:5]2[N:6]3[CH2:21][CH2:20][CH2:19][S:1][C:2]3=[N:3][C:4]=2[CH:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123141,3-DiiodopropaneHCID 178423448HCID 178423448, compound

Product 1

HCID 666281468-methyl-3,4-dihydro-2H-[1,3]thiazino[3,2-a]benzimidazoleYield 25.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask were added 2 g 2-mercapto-5-methylbenzimidazole, 4.2 g potassium carbonate, 4.0 g 1,3-diiodopropane and 60 ml N,N-dimethylformamide. The mixture was heated to 50 C under nitrogen for 5 hours and then cooled to 22 C. The reaction was quenched with 100 ml water and the product was extracted twice with ethyl acetate and washed twice with water. Following removal of the solvent, the product was recrystallized by dissolving in a hot mixture of 50 ml hexane with 10 ml 2-propanol. After cooling to 5 C, the product was filtered, washed with hexane and dried giving 0.63 g of an off-white solid.

Workup

  1. temperatureThe mixture was heated to 50 C under nitrogen for 5 hours
  2. temperaturecooled to 22 C
  3. customThe reaction was quenched with 100 ml water
  4. extractionthe product was extracted twice with ethyl acetate
  5. washwashed twice with water
  6. customremoval of the solvent
  7. customthe product was recrystallized
  8. dissolutionby dissolving in a hot mixture of 50 ml hexane with 10 ml 2-propanol
  9. temperatureAfter cooling to 5 C
  10. filtrationthe product was filtered
  11. washwashed with hexane
  12. customdried

Sources & evidence

ORD record
ord-82efc03176df4812bbd39c2761054352
Source dataset
uspto-grants-2012_05
Patent number
US08182718B2

Reaction notes

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