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

HRID 2421937Notes

Reaction equation

HRID 2421937 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[C:8](O)=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])[CH2:2][CH2:3][CH3:4].C(Cl)(=O)C([Cl:23])=O.CN(C=O)C>C(Cl)Cl>[CH2:1]([N:5]1[C:9](=[O:10])[C:8]([Cl:23])=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[S:6]1(=[O:19])=[O:18])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chloride2×HCID 67243252HCID 67243252, compound

Product 1

HCID 672426232-Butyl-4-chloro-5-phenylisothiazol-3(2H)-one 1,1-dioxideYield 92.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Butyl-4-hydroxy-5-phenylisothiazol-3(2H)-one 1,1-dioxide (444 mg, 1.58 mmol) was dissolved in dry DCM (15 mL) at rt and under an atmosphere of nitrogen. Oxalyl chloride (0.15 mL, 1.73 mmol) was added dropwise and the reaction mixture was refluxed for 1.5 h. DMF (0.08 mL) was added followed by the addition of oxalyl chloride (0.15 mL, 1.73 mmol) in 2 portions and the reaction mixture was refluxed for another 6 h. The solvents were evaporated and the residue was partitioned between water and DCM. The combined organic layers were washed with water and the two phases were separated using a phase separator. Evaporation of the organic phase gave the title compound (440 mg, 88%) as a brown oil with approximately 95% purity according to 1H-NMR and was used without further purification; 1H-NMR (400 MHz, CDCl3): δ 7.96-8.00 (m, 2H), 7.53-7.62 (m, 3H), 3.74-3.80 (t, 2H), 1.78-1.87 (m, 2H), 1.39-1-50 (m, 2H), 0.98 (t, 3H); 13C-NMR (100 MHz, CDCl3): δ 156.3, 137.1, 132.7, 129.6, 129.2, 127.6, 123.7, 40.9, 30.1, 20.1, 13.7.

Workup

  1. temperaturethe reaction mixture was refluxed for 1.5 h
  2. temperaturethe reaction mixture was refluxed for another 6 h
  3. customThe solvents were evaporated
  4. customthe residue was partitioned between water and DCM
  5. washThe combined organic layers were washed with water
  6. customthe two phases were separated
  7. customEvaporation of the organic phase

Sources & evidence

ORD record
ord-63f335e20a7b4d16a3f13553f4e063da
Source dataset
uspto-grants-2011_06
Patent number
US07960380B2

Reaction notes

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