Cesium carbonate → HCID 19424412, compound

HRID 743446Notes

Reaction equation

HRID 743446 reaction equation
[Cs+].[Cl:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:4]=1[C:5]([O-:7])=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:20][N:21]1[C:25](=[O:26])[CH:24]([CH2:27][CH2:28][CH3:29])[N:23]([CH2:30][CH3:31])[S:22]1(=[O:33])=[O:32]>CO.CN(C=O)C>[Cl:2][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]([Cl:12])[C:4]=1[C:5]([O:7][CH2:20][N:21]1[C:25](=[O:26])[CH:24]([CH2:27][CH2:28][CH3:29])[N:23]([CH2:30][CH3:31])[S:22]1(=[O:32])=[O:33])=[O:6]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 19424415HCID 19424415, compoundHCID 88140978HCID 88140978, compound

Product 1

HCID 19424412HCID 19424412, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2,6-dichlorobenzoic acid cesium salt (prepared from 0.42 g of the acid and cesium carbonate (0.36 g) in methanol followed by removal of methanol and drying in vacuo) and 2-chloromethyl-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (0.5 g) in DMF was allowed to react at 90°-100° C. for 2 hours, and then cooled. The mixture was diluted with ice/water, extracted with ether/ethyl acetate, 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 0.64 g (80%) of 2-(2,6-dichloro-phenylcarbonyloxymethyl)-4-propyl-5-ethyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: Ar=2,6-Cl2 -phenyl; R1 =H; R2 =propyl; R3 =ethyl) as an oil.

Workup

  1. customto react at 90°-100° C. for 2 hours
  2. temperaturecooled
  3. extractionextracted with ether/ethyl acetate
  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-b64ea6e045e64efe8c093fec9c62246b
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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