Dabco → HCID 20087903, compound

HRID 275321Notes

Reaction equation

HRID 275321 reaction equation
S(Cl)(Cl)(=O)=O.[Cl:6][C:7]1[CH:8]=[C:9]2[C:14](=[CH:15][CH:16]=1)[NH:13][C:12]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[S:23]CC1C=CC=CC=1)=[CH:11][C:10]2=[O:31].N12CCN(CC1)CC2>>[Cl:6][C:7]1[CH:16]=[CH:15][C:14]2[N:13]3[S:23][C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=4[C:12]3=[CH:11][C:10](=[O:31])[C:9]=2[CH:8]=1

Participants

4

Reactant 3

HCID 9237DabcoHCID 24648Sulfuryl chlorideHCID 20087902HCID 20087902, compound

Product 1

HCID 20087903HCID 20087903, compoundYield 26%

Conditions

Temperature
25 °C

Procedure

Sulfuryl chloride (0. 305 ml, 3.78 mmole, 1.0 equiv.) was added dropwise over 3 min to a suspension of 6-chloro-2-[2-[(phenylmethyl)thio]phenyl]-4(1H)-quinolinone (1.43 g, 3.78 mmole, 1 equiv.) in dry, EtOH-free CHCl3 (190 ml) at -15° C. The mixture was stirred for 0.5 hr, then was heated to reflux After 20 min, the reaction was cooled to 25° C., and 1,4-diazabicyclo[2.2.21octane (636 mg, 5.67 mmole, 1.5 equiv.) was added. The nearly homogeneous solution was stirred at 25° C. for an additional 5 min, then was washed with H2O (3×50 ml). The combined aqueous layers, which contained suspended product, were back-extracted with CHCl3, and the combined organic layers were diluted with CHCl3 (200 ml) and MeOH (50 ml) to dissolve suspended solids. Drying (MgSO4), concentration, and silica gel chromatography (CHCl3, then 10% MeOH in 50% EtOAc/CHCl3, then 10% MeOH/CHCl3) gave 3-chloro-5H-[1,2]benzisothiazolo [2,3-a]quinoline-5-one (0.28 g, 26%) as a yellow solid. Two recrystallizations from CHCl3 /EtOAc gave yellow, very fine needles: mp>350° C.; TLC (5% MeOH in 50% EtOAc/CHCl3) Rf 0.32; 1H NMR (CDCl3) δ8.52 (d, J=2.2 Hz, 1H), 8.00 (app d, 1H), 7.62-7.74 (m, 3H), 7.50-7.60 (m, 1H), 7.44 (d, J=8.8 Hz, 1H), 7.08 (s, 1H); IR (KBr) 1613, 1587, 1567, 1554, 1539, 1461, 1450 cm-1 ; MS (NH3), m/e (%) 288 (41, (37Cl M+H)+), 286 (100, (35Cl M+H)+). Anal. Calcd for C15H8ClNOS: C, 63.05; H, 2.82; N, 4.90. Found: C, 62.83; H, 2.51; N, 4.75.

Workup

  1. customin dry
  2. customat -15° C
  3. temperaturewas heated
  4. temperatureto reflux After 20 min
  5. stirringThe nearly homogeneous solution was stirred at 25° C. for an additional 5 min
  6. washwas washed with H2O (3×50 ml)
  7. extractionwere back-extracted with CHCl3
  8. additionthe combined organic layers were diluted with CHCl3 (200 ml) and MeOH (50 ml)
  9. dissolutionto dissolve
  10. customDrying
  11. concentration(MgSO4), concentration, and silica gel chromatography (CHCl3

Sources & evidence

ORD record
ord-3b5bf61bae1549b0b92520d1a66023d6
Source dataset
uspto-grants-1995_02
Patent number
US05393756

Reaction notes

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