Hydrochloric Acid → HCID 22934786, compound

HRID 902834Notes

Reaction equation

HRID 902834 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., 1994, Vol. 77, p. 1256) (2.0 g) was dissolved in methanol (100 ml), and ammonium acetate (8.2 g) and sodium cyanoborohydride (4.0 g) were added to heat the mixture under reflux for 20 hours. Hydrochloric acid was added to the reaction mixture to decompose excessive sodium cyanoborohydride before the solvent was distilled off under reduced pressure. The residue was alkalified with a 1N solution of sodium hydroxide and then extracted with methylene chloride. The resultant organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure to obtain a pale yellow oil. This oil was dissolved in methanol (50 ml), and an aqueous solution (4.29 g) of formaldehyde and sodium cyanoborohydride (3.49 g) were added to stir the mixture at room temperature for 12 hours. The solvent was distilled off under reduced pressure, and methylene chloride was added to the residue, the organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel (methylene chloride:methanol=10:1) to obtain the title compound (740 mg).

Workup

  1. temperatureto heat the mixture
  2. temperatureunder reflux for 20 hours
  3. distillationwas distilled off under reduced pressure
  4. extractionextracted with methylene chloride
  5. dry with materialThe resultant organic layer was dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customto obtain a pale yellow oil
  8. distillationThe solvent was distilled off under reduced pressure, and methylene chloride
  9. additionwas added to the residue
  10. washthe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  11. dry with materialdried over anhydrous magnesium sulfate
  12. distillationThe solvent was distilled off under reduced pressure
  13. customthe residue was purified by column chromatography on silica gel (methylene chloride:methanol=10:1)

Sources & evidence

ORD record
ord-b3f94783857d46378ec2557e5df4f07d
Source dataset
uspto-grants-2008_04
Patent number
US07365205B2

Reaction notes

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