Hydrochloric Acid → HCID 55285356, compound

HRID 601627Notes

Reaction equation

HRID 601627 reaction equation
NOS(O)(=O)=O.C(OC(=O)[NH:13][CH2:14][CH2:15][C:16](=[S:23])[N:17]=[C:18]([N:20](C)C)[CH3:19])(C)(C)C.N1C=CC=CC=1.Cl>CO.C(O)C>[CH3:19][C:18]1[N:17]=[C:16]([CH2:15][CH2:14][NH2:13])[S:23][N:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 76284hydroxylamine-O-sulfonic acidHCID 86624590HCID 86624590, compound

Product 1

HCID 55285356HCID 55285356, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 887MethanolSolvent

Procedure

Hydroxylamine-O-sulfonic acid (0.68 g, 6.0 mmol) in methanol (5 ml) is added to a stirred solution of [2-(1-Dimethylamino-ethylidenethiocarbamoyl)-ethyl]-carbamic acid tert-butyl ester (1.43 g, 5.0 mmol) and pyridine (0.83 ml, 10 mmol) in ethanol (25 ml). After stirring the reaction for 18 hours at room temperature the solvent is removed in vacuo and the residue is partitioned between water and DCM. The organic extract is separated, dried (MgSO4), and the solvent is removed to give a colourless oil which is dissolved in ethanol (20 ml). Aqueous HCl (2M, 10 ml) is added and the mixture is heated at reflux for 1 hour. After cooling to room temperature the solvent is removed. The product is dissolved in aqueous NaHCO3 and the free base is extracted with ethyl acetate. The organic extract is dried (MgSO4) and the solvent removed to give the titled compound.

Workup

  1. customthe reaction for 18 hours at room temperature the solvent
  2. customis removed in vacuo
  3. customthe residue is partitioned between water and DCM
  4. extractionThe organic extract
  5. customis separated
  6. dry with materialdried (MgSO4)
  7. customthe solvent is removed
  8. customto give a colourless oil which
  9. temperaturethe mixture is heated
  10. temperatureat reflux for 1 hour
  11. customis removed
  12. dissolutionThe product is dissolved in aqueous NaHCO3
  13. extractionthe free base is extracted with ethyl acetate
  14. extractionThe organic extract
  15. dry with materialis dried (MgSO4)
  16. customthe solvent removed

Sources & evidence

ORD record
ord-8027576bd8f64887aabc96b4a8049665
Source dataset
uspto-grants-2011_03
Patent number
US07902375B2

Reaction notes

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