Thiophosgene → HCID 88157933, compound

HRID 1597800Notes

Reaction equation

HRID 1597800 reaction equation
[C:1](=[O:4])([O-])O.[Na+].[C:6](Cl)(Cl)=[S:7].[S:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[CH2:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1>C(Cl)Cl>[S:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[C:11]1[CH2:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH:25][C:6](=[S:7])[O:4][CH3:1])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 18932285HCID 18932285, compound

Product 1

HCID 88157933HCID 88157933, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

20.8 ml of sodium hydrogencarbonate and 0.05 ml of thiophosgen were added to a solution of 50.2 mg of 4-(benzothiazol-2-ylmethoxy)aniline [prepared as described in Example 3 (b)] in 2 ml of methylene chloride and the resulting mixture was stirred at room temperature for 2 hours. 8 ml of methylene chloride were then added to the reaction mixture and the resulting mixture was washed with water and the organic fraction then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting residue was then dissolved in 3 ml of tetrahydrofuran and 0.01 ml of methanol. 13.2 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to the resulting mixture which was then stirred at room temperature for 30 minutes. At the end of this time, 5 mg of sodium methoxide were added to the reaction mixture which was then stirred for 30 minutes. A saturated aqueous sodium chloride solution was then added to the reaction mixture and the resulting mixture was extracted with ethyl acetate. The resulting extract was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure and the resulting residue was recrystallized from a mixed solvent of ethyl acetate and hexane to give 49.7 mg (yield 76%) of the title compound as a solid having a melting point of 160°-162° C.

Workup

  1. washthe resulting mixture was washed with water
  2. dry with materialthe organic fraction then dried over anhydrous sodium sulfate
  3. customThe solvent was removed by evaporation under reduced pressure
  4. dissolutionthe resulting residue was then dissolved in 3 ml of tetrahydrofuran
  5. addition13.2 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to the resulting mixture which
  6. stirringwas then stirred at room temperature for 30 minutes
  7. additionAt the end of this time, 5 mg of sodium methoxide were added to the reaction mixture which
  8. stirringwas then stirred for 30 minutes
  9. additionA saturated aqueous sodium chloride solution was then added to the reaction mixture
  10. extractionthe resulting mixture was extracted with ethyl acetate
  11. extractionThe resulting extract
  12. washwas washed with a saturated aqueous sodium chloride solution
  13. dry with materialdried over anhydrous sodium sulfate
  14. customThe solvent was removed by evaporation under reduced pressure
  15. customthe resulting residue was recrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-a58460c80aba442387357373a979089d
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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