Hydrochloric Acid → HCID 22934786, compound

HRID 2104349Notes

Reaction equation

HRID 2104349 reaction equation
[Cl:1][C:2]1[S:3][C:4]2[CH2:10][C:9](=O)[CH2:8][CH2:7][C:5]=2[N:6]=1.C([O-])(=O)C.[NH4+].[C:17]([BH3-])#[N:18].[Na+].Cl.[CH2:22]=O>CO>[Cl:1][C:2]1[S:3][C:4]2[CH2:10][CH:9]([N:18]([CH3:17])[CH3:22])[CH2:8][CH2:7][C:5]=2[N:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydride3×HCID 552531102-Chloro-4,7-dihydro-1,3-benzothiazol-6(5H)-one

Product 1

HCID 22934786HCID 22934786, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

2-Chloro-4,7-dihydro-1,3-benzothiazol-6(5H)-one (Helv. Cim. Acta., vol. 77, p. 1256 (1994)) (2.0 g) was dissolved in methanol (100 mL), and to the solution were added ammonium acetate (8.2 g) and sodium cyanoborohydride (4.0 g), followed by heating under reflux for 20 hours. Hydrochloric acid was added to the reaction mixture, to thereby decompose excess sodium cyanoborohydride, and the solvent was distilled away under reduced pressure. A 1N sodium hydroxide solution was added to the residue, to thereby make the mixture alkaline. The mixture was extracted with methylene chloride. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled away under reduced pressure, to thereby give a pale-yellow oily matter. This oily matter was dissolved in methanol (50 mL), and to the solution were added aqueous formaldehyde (4.29 g) and sodium cyanoborohydride (3.49 g), followed by stirring at room temperature for 12 hours. The solvent was distilled away under reduced pressure, and methylene chloride was added to the residue. The thus-obtained mixture was washed with saturated sodium hydrogencarbonate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (methylene chloride:methanol=10:1), to thereby give the title compound (740 mg).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 20 hours
  3. distillationthe solvent was distilled away under reduced pressure
  4. additionA 1N sodium hydroxide solution was added to the residue
  5. extractionThe mixture was extracted with methylene chloride
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled away under reduced pressure
  8. customto thereby give a pale-yellow oily matter
  9. distillationThe solvent was distilled away under reduced pressure, and methylene chloride
  10. additionwas added to the residue
  11. washThe thus-obtained mixture was washed with saturated sodium hydrogencarbonate
  12. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  13. distillationThe solvent was distilled away under reduced pressure
  14. customthe residue was purified by silica gel column chromatography (methylene chloride:methanol=10:1)

Sources & evidence

ORD record
ord-e25ee1d2a77d4289a65341c24c92b9ec
Source dataset
uspto-grants-2009_08
Patent number
US07576135B2

Reaction notes

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