Water → HCID 10590421, compound

HRID 1599388Notes

Reaction equation

HRID 1599388 reaction equation
[C:1]([N:9]1[CH2:14][CH2:13][C:12](Cl)=[C:11]([C:16]2[C:17](Cl)=[N:18][S:19][N:20]=2)[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.[SH2:23].[Na].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([N:9]1[CH2:14][CH2:13][C:12]2[S:23][C:17]3[C:16](=[N:20][S:19][N:18]=3)[C:11]=2[CH2:10]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10688490HCID 10688490, compoundHCID 53442613Sodium hydrogen sulfide hydrate

Product 1

HCID 10590421HCID 10590421, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-benzoyl-4-chloro-3-(3-chloro-1,2,5-thiadiazol-4-yl)-1,2,5,6-tetrahydropyridine (3.4 g, 10 mmol) in dimethylformamide was added sodiumhydrogensulfide monohydrate (1.5 g, 20 mmol) and potassium carbonate (2.0 g). The reaction mixture was stirred at room temperature for 3 h. Water (500 ml) was added and the water phase was extracted with diethylether (2×15 ml). The organic extracts were dried over magnesium sulfate, filtered and evaporated. The residue was purified by column chromatography, eluent: methylene chloride/ethyl acetate: 10/1, giving the title compound in 2.1 g yield.

Workup

  1. extractionthe water phase was extracted with diethylether (2×15 ml)
  2. dry with materialThe organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography, eluent

Sources & evidence

ORD record
ord-c3fad007ab1742f6b9b47791d87b723c
Source dataset
uspto-grants-1998_04
Patent number
US05741788

Reaction notes

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