2,6-Dichlorobenzoic acid → 2-(2,6-Dichlorophenylcarbonyloxy-methyl)-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

HRID 743436Notes

Reaction equation

HRID 743436 reaction equation
Cl[CH2:2][N:3]1[C:7](=[O:8])[CH:6]([CH2:9][CH2:10][CH3:11])[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(N(CC)CC)C>C1(C)C=CC=CC=1>[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]([CH2:9][CH2:10][CH3:11])[N:5]([CH3:12])[S:4]1(=[O:14])=[O:13])=[O:19]

Participants

5

Reactant 3

HCID 57582,6-Dichlorobenzoic acidHCID 8471TriethylamineHCID 158374782-Chloromethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide

Product 1

HCID 158380712-(2,6-Dichlorophenylcarbonyloxy-methyl)-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxideYield 80.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-chloromethyl-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (0.5 g; 2.08 mmol), 2,6-dichlorobenzoic acid (0.4 g; 2.09 mmol), and triethylamine (0.3 mL; 2.08 mmol) in 20 ml of toluene was allowed to react at 90°-100° C. for 15 hours and at 100° C. for 19 hours, and then cooled. The mixture was concentrated in vacuo and the residue was purified by flesh chromatography to afford 0.66 g (80%) of 2-(2,6-dichlorophenylcarbonyloxy-methyl)-4-propyl-5-methyl-1,2,5-thiadiazolidin-3-one 1,1-dioxide (Formula I: Ar=2,6-Cl2 -phenyl; R1 =H; R2 =propyl; R3 =methyl) as an oil.

Workup

  1. customto react at 90°-100° C. for 15 hours and at 100° C. for 19 hours
  2. temperaturecooled
  3. concentrationThe mixture was concentrated in vacuo
  4. customthe residue was purified by flesh chromatography

Sources & evidence

ORD record
ord-4e9f29e892d1482fade5a40bb3a58949
Source dataset
uspto-grants-1996_09
Patent number
US05556909

Reaction notes

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