Water → HCID 784990, compound

HRID 1029364Notes

Reaction equation

HRID 1029364 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([SH:10])=[N:7][C:6]=2[CH:11]=1.[CH2:12](N(CC)CC)[CH3:13].ICC.O>C(O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([S:10][CH2:12][CH3:13])=[N:7][C:6]=2[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 8471TriethylamineHCID 178527796HCID 178527796, compound

Product 1

HCID 784990HCID 784990, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Chloro-2-mercaptobenzothiazole (20.17 g, 0.1 mol) in 55 ml 95% ethanol was treated with 10.1 g (0.1 mol) triethylamine to give a brown solution. Iodoethane (15.6 g, 0.1 mol) was added and the mixture refluxed 67 minutes. The mixture was cooled and poured into 300 ml water to precipitate a solid. The aqueous phase was extracted 3×50 ml methylene chloride. The organic extracts were combined with solid precipitate, washed with water, dried over Na2SO4, filtered, and rotary evaporated to give brown solid. Recrystallization from isopropanol yielded 12.26 g (53%) brown crystals, mp 49°-50° C.

Workup

  1. customto give a brown solution
  2. temperaturethe mixture refluxed 67 minutes
  3. temperatureThe mixture was cooled
  4. customto precipitate a solid
  5. extractionThe aqueous phase was extracted 3×50 ml methylene chloride
  6. washwashed with water
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customrotary evaporated
  10. customto give brown solid
  11. customRecrystallization from isopropanol

Sources & evidence

ORD record
ord-e976a73932d74feaa72b1951acff29a2
Source dataset
uspto-grants-1992_04
Patent number
US05102781

Reaction notes

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