1-Decanethiol → 1,3-Dioxo-6-(decylthio)-1H-benz[de]isoquinoline-2(3H)-acetic acid

HRID 126686

Reaction equation

HRID 126686 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:20])[N:7]([CH2:16][C:17]([OH:19])=[O:18])[C:8](=[O:15])[C:9]3[C:14]=2[C:13]=1[CH:12]=[CH:11][CH:10]=3.[CH2:21]([SH:31])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O>[O:15]=[C:8]1[C:9]2[C:14]3[C:13](=[C:2]([S:31][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:3]=[CH:4][C:5]=3[C:6](=[O:20])[N:7]1[CH2:16][C:17]([OH:19])=[O:18])[CH:12]=[CH:11][CH:10]=2

Participants

5

Reactant 3

HCID 89171-DecanethiolHCID 10340Sodium CarbonateHCID 150089276-chloro-1,3-dioxo-1H-benz[de]isoquinoline-2(3H)-acetic acid

Product 1

HCID 202878141,3-Dioxo-6-(decylthio)-1H-benz[de]isoquinoline-2(3H)-acetic acidYield 60.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a nitrogen atmosphere, a suspension of 6-chloro-1,3-dioxo-1H-benz[de]-isoquinoline-2(3H)-acetic acid (5.0 g, 17.3 mmoles, described in Example 2), 1-decanethiol (3.3 g, 3.9 ml, 19 mmoles) and anhydrous sodium carbonate (2.4 g, 17.3 mmoles) in dimethylformamide (150 ml) was stirred and heated at reflux for 15 minutes. After cooling the precipitate was collected by filtration and then dissolved in water. The solution was acidified with 2 N hydrochloric acid and extracted with ethyl acetate. The extract was dried (MgSO4) and evaporated to dryness the oily residue was triturated with hexane. The solid was recrystallized from benzene-hexane to give 4.50 g of the title product; mp 137°-140° C.; UV (MeOH) 257, 329, 343 and 382, ε=16,375, 2,849, 4,929 and 15,820, respectively; IR (CHCl3) δ2900, 1725 (inflection), 1698, 1662 cm-1 ; NMR (CDCl3) 0.85 (t, 3H, J=5), 1.25 (m, 16H), 3.1 (t, 2H, J=6.5), 4.92 (s, 2H), 8.45 (m, 3H), 9.75 (broad, 1H); Anal. Calc'd: C, 67.42%; H, 6.84%; N, 3.28%; Found: C, 67.17%; H, 6.84%; N, 3.21%.

Workup

  1. temperatureheated
  2. temperatureat reflux for 15 minutes
  3. temperatureAfter cooling the precipitate
  4. filtrationwas collected by filtration
  5. dissolutiondissolved in water
  6. extractionextracted with ethyl acetate
  7. dry with materialThe extract was dried (MgSO4)
  8. customevaporated to dryness the oily residue
  9. customwas triturated with hexane
  10. customThe solid was recrystallized from benzene-hexane

Sources & evidence

ORD record
ord-a7e1f87363c8430d8b1727ce54743234
Source dataset
uspto-grants-1981_03
Patent number
US04254109

Linked notes

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