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

HRID 729256Notes

Reaction equation

HRID 729256 reaction equation
[CH2:1]([N:5]1[C:9](=[O:10])[C:8](O)=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[S:6]1(=[O:20])=[O:19])[CH2:2][CH2:3][CH3:4].CN(C=O)C.C(Cl)(=O)C([Cl:29])=O>C(Cl)Cl>[CH2:1]([N:5]1[C:9](=[O:10])[C:8]([Cl:29])=[C:7]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[S:6]1(=[O:20])=[O:19])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 686623342-Butyl-5-(4-chlorophenyl)-4-hydroxyisothiazol-3(2H)-one 1,1-dioxide

Product 1

HCID 686627162-Butyl-4-chloro-5-(4-chlorophenyl)isothiazol-3(2H)-one 1,1-dioxideYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Butyl-5-(4-chlorophenyl)-4-hydroxyisothiazol-3(2H)-one 1,1-dioxide (0.9 g, ca. 60%, 1.71 mmol) was dissolved in DCM (50 mL). DMF (0.13 mL) was added. Under nitrogen atmosphere, oxalyl chloride (0.434 g, 3.42 mmol) was dropped in. The mixture was then heated to reflux for 2 h and then evaporated to dry. Water (30 mL) was added into the residue. It was then extracted with DCM (20 mL×3). The extracts were combined and washed with water (50 mL×3) and brine (20 mL), dried (MgSO4) and evaporated. The residue was then purified by column chromatography (ISOLUTE SI, 20 g/70 mL), eluting with DCM:heptane (25:75), to give the title compound (0.496 g, 87%); 1H NMR (400 MHz, CDCl3): δ 7.93 (d, 2H), 7.54 (d, 2H), 3.76 (t; 2H), 1.85-1.77 (m, 2H), 1.48-1.39 (m, 2H), 0.98 (t, 3H); 13C NMR (100 MHz, CDCl3): δ 155.8, 142.4, 139.0, 130.2, 129.9, 127.7, 121.8, 40.8, 30.2, 19.9, 13.4.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 2 h
  3. customevaporated
  4. customto dry
  5. additionWater (30 mL) was added into the residue
  6. extractionIt was then extracted with DCM (20 mL×3)
  7. washwashed with water (50 mL×3) and brine (20 mL)
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customThe residue was then purified by column chromatography (ISOLUTE SI, 20 g/70 mL)
  11. washeluting with DCM:heptane (25:75)

Sources & evidence

ORD record
ord-7295aa4174bf48778bf68afaed4f452b
Source dataset
uspto-grants-2009_09
Patent number
US07582629B2

Reaction notes

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