Hydrochloric Acid → HCID 18932285, compound

HRID 1597776Notes

Reaction equation

HRID 1597776 reaction equation
Cl.[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][CH:14]=1.[OH-].[Na+]>C(O)C>[S:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 313Hydrochloric Acid2×HCID 14798Sodium HydroxideHCID 590751HCID 590751, compound

Product 1

HCID 18932285HCID 18932285, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15 ml of concentrated hydrochloric acid were carefully added to 4.99 g of O-(benzothiazol-2-ylmethyl)-4-nitrophenol [prepared as described in step (a) above] suspended in 100 ml of ethanol, with ice cooling, after which 8.26 g of stannous chloride were added in small portions to the resulting mixture at the same temperature. The temperature of the reaction mixture was then elevated to room temperature and the mixture stirred for 30 minutes at this temperature, before elevating the temperature further to 50° C. and stirring at this new temperature for a further 1.5 hours. At the end of this time 15 ml of concentrated hydrochloric acid and 8.26 g of stannous chloride were added to the reaction mixture and the resulting mixture was then stirred at 50° C. for 4 hours. The reaction mixture was then allowed to cool to room temperature, after which a saturated aqueous sodium hydroxide solution was added to the reaction mixture to adjust it to pH 10 and the resulting mixture was extracted with ethyl acetate. The resulting extract was washed with water, dried over anhydrous sodium sulfate and the solvent was removed by evaporation under reduced pressure to give a crude crystalline solid which was washed with a 10:1 by volume mixture of hexane and ethyl acetate to give 1.92 g (yield 43%) of the title compound as a solid having a melting point of 87° to 90° C.

Workup

  1. customwas then elevated to room temperature
  2. customfurther to 50° C.
  3. stirringstirring at this new temperature for a further 1.5 hours
  4. stirringthe resulting mixture was then stirred at 50° C. for 4 hours
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. extractionThe resulting extract
  7. washwas washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was removed by evaporation under reduced pressure
  10. customto give a crude crystalline solid which
  11. washwas washed with a 10:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-3d4e82e4f0ec474894bfd0e82229fc96
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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