Benzyl Bromide → 5-(benzylthio)-N-methyl-1,3,4-thiadiazol-2-amine

HRID 1391191Notes

Reaction equation

HRID 1391191 reaction equation
[O-]CC.[Na+].[CH3:5][NH:6][C:7]1[S:8][C:9]([SH:12])=[N:10][N:11]=1.[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[CH3:5][NH:6][C:7]1[S:8][C:9]([S:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:10][N:11]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 2723922Sodium ethoxideHCID 178482505HCID 178482505, compound

Product 1

HCID 8051175-(benzylthio)-N-methyl-1,3,4-thiadiazol-2-amineYield 59.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium ethoxide in ethanol (prepared by adding 13.5 g of anhydrous sodium methoxide to 300 ml of absolute ethanol) was added 31 g of 2-methylamino-5-mercapto-1,3,4-thiadiazole. After stirring for 15 min. at room temperature, 36 g of benzyl bromide was added to the homogeneous solution and the reaction heated to reflux of 4 hrs. At the end of the reflux period, most of the ethanol was removed at reduced pressure, water was added and the reaction extracted with ethyl acetate, which was washed with water and saturated NaCl, then dried over Na2SO4. Removal of the solvent gave a viscous oil which was crystallized from a mixture of ether and petroleum ether to give 29.7 g of 2-methylamino-5-benzylthio-1,3,4-thiadiazole, MP 87°-89° C.

Workup

  1. temperaturethe reaction heated
  2. temperatureto reflux of 4 hrs
  3. customAt the end of the reflux period, most of the ethanol was removed at reduced pressure, water
  4. additionwas added
  5. extractionthe reaction extracted with ethyl acetate, which
  6. washwas washed with water and saturated NaCl
  7. dry with materialdried over Na2SO4
  8. customRemoval of the solvent
  9. customgave a viscous oil which
  10. customwas crystallized from a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-00c8035261d942aca2f700a1438de82b
Source dataset
uspto-grants-1979_02
Patent number
US04141717

Reaction notes

Loading…