2,6-Dichlorobenzoic acid → HCID 15838070, compound

HRID 743427Notes

Reaction equation

HRID 743427 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([OH:6])=[O:5].Cl[CH2:13][N:14]1[C:18](=[O:19])[CH:17]([CH:20]([CH3:22])[CH3:21])[NH:16][S:15]1(=[O:24])=[O:23].C(N(CC)CC)C>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[C:3]=1[C:4]([O:6][CH2:13][N:14]1[C:18](=[O:19])[CH:17]([CH:20]([CH3:21])[CH3:22])[NH:16][S:15]1(=[O:23])=[O:24])=[O:5]

Participants

5

Reactant 3

HCID 57582,6-Dichlorobenzoic acidHCID 8471TriethylamineHCID 19424446HCID 19424446, compound

Product 1

HCID 15838070HCID 15838070, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2,6-dichlorobenzoic acid (0.44 g; 2.3 mmol), 2-chloromethyl-4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (0.5 g; 2.2 mmol) and triethylamine (230 mg; 2.3 mmol) in toluene was allowed to reflux for 2.5 hours, and then cooled. The mixture was concentrated in vacuo and the residue was purified by flash silica gel chromatography (25%-30% ethyl acetate in hexane) to afford 0.41 g (49%) of 2-(2,6-dichlorophenylcarbonyloxymethyl)-4-isopropyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: Ar=2,6-Cl2 -phenyl; R1 =H; R2 =isopropyl; R3 =H) as a solid, m.p.151°-152° C.

Workup

  1. temperatureto reflux for 2.5 hours
  2. temperaturecooled
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was purified by flash silica gel chromatography (25%-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-6096182b1fed4ce897bb1f8d0a5b6bfc
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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