Benzyl Bromide → 2-Phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 1736311Notes

Reaction equation

HRID 1736311 reaction equation
[CH:1]([CH:4]1[NH:8][S:7](=[O:10])(=[O:9])[NH:6][C:5]1=[O:11])(C)[CH3:2].[C:12]1([CH2:18]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:20]1(C)C=CC=CC=1.CN(C=O)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:12]1([CH2:18][N:6]2[C:5](=[O:11])[CH:4]([CH2:1][CH2:2][CH3:20])[NH:8][S:7]2(=[O:10])=[O:9])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 194244514-Isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideHCID 21735183Dimethylformamide toluene

Product 1

HCID 189222572-Phenylmethyl-4-propyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 72%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

Eight grams (44.94 mmol) of 4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (which was dissolved in methanol, brought to pH 5 with ion exchange resin, filtered, and concentrated in vacuo to remove methanol), phenylmethyl bromide (8.09 g, 47.2 mmol), and tetrabutylammonium bromide (1.5 g, 4.66 mmol) suspended in toluene/DMF (200 ml/50 ml) was allowed to react at 130° C. for 30 hours. The resulting mixture was cooled, the excess toluene was concentrated in vacuo, and the residue was diluted with 200 ml of water and extracted with ether/ethyl acetate (4:1, 700 ml). The organic layer was washed with water and brine, dried and concentrated in vacuo to yield a residue which was purified by flash chromatography to afford 8.6 g (72%) of 2-phenylmethyl-4-isopropyl-1,2,5-thiadiazol-idin-3-one 1,1-dioxide (Formula IX: R1 =H; R2 =isopropyl) as a solid.

Workup

  1. customto react at 130° C. for 30 hours
  2. temperatureThe resulting mixture was cooled
  3. concentrationthe excess toluene was concentrated in vacuo
  4. additionthe residue was diluted with 200 ml of water
  5. extractionextracted with ether/ethyl acetate (4:1, 700 ml)
  6. washThe organic layer was washed with water and brine
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customto yield a residue which
  10. customwas purified by flash chromatography

Sources & evidence

ORD record
ord-d1941fb923fa480eab4ed3928086a509
Source dataset
uspto-grants-1996_07
Patent number
US05541168

Reaction notes

Loading…