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

HRID 743437Notes

Reaction equation

HRID 743437 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, 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-8f905c599f9e42a5ae93696785f40892
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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