2,6-Dichlorobenzoic acid → HCID 19424407, compound

HRID 743441Notes

Reaction equation

HRID 743441 reaction equation
Cl[CH2:2][N:3]1[C:7](=[O:8])[CH:6]([CH:9]([CH3:11])[CH3:10])[N:5]([CH3:12])[S:4]1(=[O:14])=[O:13].[Cl:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:17]=1[C:18]([OH:20])=[O:19].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[Cl:15][C:16]1[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[C:17]=1[C:18]([O:20][CH2:2][N:3]1[C:7](=[O:8])[CH:6]([CH:9]([CH3:11])[CH3:10])[N:5]([CH3:12])[S:4]1(=[O:14])=[O:13])=[O:19]

Participants

6

Reactant 3

HCID 57582,6-Dichlorobenzoic acidHCID 11430Potassium CarbonateHCID 19424418HCID 19424418, compound

Product 1

HCID 19424407HCID 19424407, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloromethyl-4-isopropyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (0.5 g; 2.08 mmol) in 10 ml of DMF was added at room temperature 2,6-dichlorobenzoic acid (0.44 g; 2.3 mmol), potassium carbonate (0.43 g, 3.1 mmol), and tetrabutylammonium bromide (67 mg; 0.21 mmol) and the resulting solution was allowed to react at 60°-70° C. for 2 hours and then cooled. The mixture was diluted with ice/water, extracted with ether/ethyl acetate (5:1, 400 ml), and the organic layer was washed with water, brine, and dried. The organic solution was concentrated in vacuo and the residue was purified by flash chromatography to afford 0.51 g (62%) of 2-(2,6-dichlorophenylcarbonyloxymethyl)-4-isopropyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: Ar=2,6-Cl2 -phenyl; R1 =H; R2 =isopropyl; R3 =methyl) as a solid, m.p. 70°-71.5° C.

Workup

  1. customto react at 60°-70° C. for 2 hours
  2. temperaturecooled
  3. extractionextracted with ether/ethyl acetate (5:1, 400 ml)
  4. washthe organic layer was washed with water, brine
  5. customdried
  6. concentrationThe organic solution was concentrated in vacuo
  7. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-5f175ede65a7406c948805e6b74a7b3a
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

Loading…