Sodium Hydroxide → 2-Methyl-5-benzoylthiomethyl-1,3,4-thiadiazole

HRID 992694Notes

Reaction equation

HRID 992694 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+].Cl[CH2:17][C:18]1[S:19][C:20]([CH3:23])=[N:21][N:22]=1.[OH-].[Na+]>CN(C=O)C.C(OCC)(=O)C.O>[CH3:17][C:18]1[S:19][C:20]([CH2:23][S:8][C:1](=[O:9])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:21][N:22]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 155820072-(Chloromethyl)-5-methyl-1,3,4-thiadiazoleHCID 23665647Potassium tert-butoxideHCID 178526132HCID 178526132, compound

Product 1

HCID 184116042-Methyl-5-benzoylthiomethyl-1,3,4-thiadiazole

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Under nitrogen atomosphere, thiobenzoic acid (2.52 ml) was added dropwise to a solution of potassium tert-butoxide (2.30 g) in DMF (15 ml) under ice cooling. After stirring for 10 minutes, 2-chloromethyl-5-methyl-1,3,4-thiadiazole in DMF (15 ml) was added to the mixture. The whole mixture was and stirred for 45 minutes. The mixture was poured into a mixture of water and ethyl acetate, and the pH was adjusted to 8.5 with 30% aqueous sodium hydroxide. Organic layer was separated, was washed with water and brine, and dried over magnesium sulfate. After evaporation of the solvent, the residue was purified on silica gel (eluent: n-hexane-ethyllactate) to afford 2-methyl-5-benzoylthiomethyl-1,3,4-thiadiazole.

Workup

  1. stirringstirred for 45 minutes
  2. customOrganic layer was separated
  3. washwas washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of the solvent
  6. customthe residue was purified on silica gel (eluent: n-hexane-ethyllactate)

Sources & evidence

ORD record
ord-3151123e922d40178cc0b9f9a7e29952
Source dataset
uspto-grants-2002_10
Patent number
US06468995B1

Reaction notes

Loading…