Dimethylformamide → 2-Butyl-4-chloro-5-(3-chlorophenyl)isothiazol-3(2H)-one 1,1-dioxide

HRID 729250Notes

Reaction equation

HRID 729250 reaction equation
CN(C=O)C.[CH2:6]([N:10]1[C:14](=[O:15])[C:13](O)=[C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[S:11]1(=[O:25])=[O:24])[CH2:7][CH2:8][CH3:9].C(Cl)(=O)C([Cl:29])=O>C(Cl)Cl>[CH2:6]([N:10]1[C:14](=[O:15])[C:13]([Cl:29])=[C:12]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=2)[S:11]1(=[O:25])=[O:24])[CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 68661999HCID 68661999, compound

Product 1

HCID 686616252-Butyl-4-chloro-5-(3-chlorophenyl)isothiazol-3(2H)-one 1,1-dioxideYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dry DMF (0.17 mL, 2.21 mmol) was added to a solution of 2-butyl-5-(3-chlorophenyl)-4-hydroxyisothiazol-3(2H)-one 1,1-dioxide (697 mg, 2.21 mmol) in dry DCM (15 mL) at rt and under an atmosphere of nitrogen. Oxalyl chloride (0.37 mL, 4.41 mmol) was added dropwise and the mixture was heated to reflux for 2.5 h. The reaction mixture was evaporated to dryness. The residue was dissolved in EtOAc and it was washed with several portions of water, dried with MgSO4, and evaporated to give the title compound (685 mg, 84%) as a brown oil which was used without further purification; 1H NMR (500 MHz, CDCl3): δ 7.96 (t, 1H), 7.84-7.88 (m, 1H), 7.57-7.61 (m, 1H), 7.50-7.55 (t, 1H), 3.79 (t, 2H), 1.80-1.87 (m, 2H), 1.39-1.51 (m, 2H), 1.00 (t, 3H); 13C NMR (125 MHz, CDCl3): δ 161.5, 155.9, 142.4, 135.8, 132.8, 131.0, 129.0, 127.3, 125.1, 41.0, 30.4, 20.1, 13.7.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 2.5 h
  3. customThe reaction mixture was evaporated to dryness
  4. dissolutionThe residue was dissolved in EtOAc
  5. washit was washed with several portions of water
  6. dry with materialdried with MgSO4
  7. customevaporated

Sources & evidence

ORD record
ord-1ac7ccacb6d04ebdb4c16d45345a8343
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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