Hydrochloric Acid → HCID 54490552, compound

HRID 1460191Notes

Reaction equation

HRID 1460191 reaction equation
Cl.[N+:2]([C:5]1[CH:21]=[CH:20][CH:19]=[CH:18][C:6]=1[CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:14]([S:16][CH3:17])=[S:15])[CH2:10][CH2:9]1)([O-])=O.O.O.Cl[Sn]Cl>C(O)C>[NH2:2][C:5]1[CH:21]=[CH:20][CH:19]=[CH:18][C:6]=1[CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:14]([S:16][CH3:17])=[S:15])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 61436Stannous chloride dihydrateHCID 19388496HCID 19388496, compound

Product 1

HCID 54490552HCID 54490552, compoundYield 77.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a mixture of 4 ml of conc. hydrochloric acid and 4 ml of ethanol was added 622 mg (2.0 mmol.) of methyl 4-(2-nitrobenzyl)-1-piperazinecarbodithioate. The mixture was chilled with ice, and then to this chilled mixture was dropwise added under stirring a solution of 2.7 g (12 mmol.) of SnCl2.2H2O in 5 ml of ethanol for 15 min. After the addition was complete, the mixture was further stirred at room temperature for 2 hours. Ethanol was distilled off under reduced pressure, and to the residue were added 10 ml of water and 10 ml of ethyl acetate. The resulting mixture was made alkaline by addition of saturated aqueous sodium hydrogen carbonate solution. Precipitated insolubles were removed by filtration. The organic filtrate was washed with a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and placed under reduced pressure to distill off the solvent. The residue was crystallized from ether, and collected by filtration, yielding 436 mg of the desired compound as a white crystalline product, m.p. 110°-113.5° C., yield 77.6%.

Workup

  1. temperatureThe mixture was chilled with ice
  2. additionto this chilled mixture was dropwise added
  3. additionAfter the addition
  4. distillationEthanol was distilled off under reduced pressure
  5. additionto the residue were added 10 ml of water and 10 ml of ethyl acetate
  6. additionby addition of saturated aqueous sodium hydrogen carbonate solution
  7. customPrecipitated insolubles were removed by filtration
  8. washThe organic filtrate was washed with a saturated aqueous sodium chloride solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationto distill off the solvent
  11. customThe residue was crystallized from ether
  12. filtrationcollected by filtration

Sources & evidence

ORD record
ord-3bae2c4eb4cb402fbe9f49c50c5b63ee
Source dataset
uspto-grants-1991_12
Patent number
US05070089

Reaction notes

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