Sodium Bicarbonate → HCID 18411620, compound

HRID 992684Notes

Reaction equation

HRID 992684 reaction equation
[C:1]([OH:9])(=[S:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].CS(O[CH2:21][C:22]1[S:26][N:25]=[N:24][C:23]=1[CH3:27])(=O)=O.C(=O)([O-])O.[Na+]>CN(C=O)C.C(OCC)(=O)C>[C:1]([S:8][CH2:21][C:22]1[S:26][N:25]=[N:24][C:23]=1[CH3:27])(=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 184116401,2,3-Thiadiazole-5-methanol, 4-methyl-, 5-methanesulfonateHCID 23665647Potassium tert-butoxideHCID 178526132HCID 178526132, compound

Product 1

HCID 18411620HCID 18411620, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Under nitrogen atmosphere, 6.64 ml (56.5 m mol) of thiobenzoic acid was added to a stirred solution of potassium tert-butoxide (6.07 g, 54.1 m mol) in DMF (80 ml) at 0° C. After stirring for 10 minutes, 5-methanesulfonyloxymethyl-4-methyl-1,2,3-thiadiazole (9.8 g, 47.0 m mol) in DMF (30 ml) was added to the mixture slowly at the same temperature. The whole mixture was stirred at 80° C. for 2 hours, poured into a mixture of diluted aqueous sodium hydrogen carbonate and ethyl acetate. Aqueous layer was separated, the organic layer was washed with brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was treated on silica gel (eluent: n-hexane/ethyl acetate=9/1-8/2) to afford 5-benzoylthiomethyl-4-methyl-1,2,3-thiadiazole (7.51 g).

Workup

  1. stirringThe whole mixture was stirred at 80° C. for 2 hours
  2. customAqueous layer was separated
  3. washthe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. additionthe residue was treated on silica gel (eluent: n-hexane/ethyl acetate=9/1-8/2)

Sources & evidence

ORD record
ord-32a958d8ed9b477aabebbf3f49b0d0c5
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

Loading…