Ethanol → HCID 54309330, compound

HRID 126689Notes

Reaction equation

HRID 126689 reaction equation
[O:1]=[C:2]1[C:11]2[C:6]3[C:7](=[C:12]([S:15][C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:13]=[CH:14][C:5]=3[C:4](=[O:22])[N:3]1[CH2:23][C:24]([OH:26])=[O:25])[CH:8]=[CH:9][CH:10]=2.[CH2:27](O)[CH3:28].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:27]([O:25][C:24](=[O:26])[CH2:23][N:3]1[C:4](=[O:22])[C:5]2[CH:14]=[CH:13][C:12]([S:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:7]3[C:6]=2[C:11](=[CH:10][CH:9]=[CH:8]3)[C:2]1=[O:1])[CH3:28]

Participants

5

Reactant 3

HCID 702EthanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 20287800HCID 20287800, compound

Product 1

HCID 54309330HCID 54309330, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1,3-Dioxo-6-(phenylthio)-1H-benz[de]isoquinoline-2(3H)-acetic acid (3.55 g, 9.77 mmoles; described in Example 1), anhydrous pure ethanol (12 ml), toluene (30 ml) and p-toluenesulfonic acid hydrate (0.2 g) were heated at reflux for 16 hr in a Soxhlet apparatus in which the thimble was filled with hydrated alkali-aluminium silicate (3 A Molecular Sieves). The resulting clear mixture was washed with water (2×80 ml), 5% sodium bicarbonate (2×80 ml) and brine (100 ml), dried (MgSO4) and concentrated to dryness. The residue was crystallized from isopropyl ether-carbon tetrachloride (1:1, 60 ml) to give 2.85 g of the title compound; mp 132°-134° C.; UV (MeOH) 231 and 344 nm, ε=25,170 and 7,360 respectively; IR (CHCl3) 1743, 1695 and 1660 cm-1 ; NMR (CDCl3) δ1.25 (t, 3H, J=7 Hz), 4.15 (q, 2H, J=7 Hz), 4.85 (s, 2H), 7.15-8.65 (m, 10H); Anal. Calc'd.: C, 67.50%; H, 4.38%; N, 3.58%; Found: C, 67.87%; H, 4.44%; N, 3.50%.

Workup

  1. temperatureat reflux for 16 hr in a Soxhlet apparatus in which the thimble
  2. washThe resulting clear mixture was washed with water (2×80 ml), 5% sodium bicarbonate (2×80 ml) and brine (100 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated to dryness
  5. customThe residue was crystallized from isopropyl ether-carbon tetrachloride (1:1, 60 ml)

Sources & evidence

ORD record
ord-f87845836a6449399008d1f01306de1c
Source dataset
uspto-grants-1981_03
Patent number
US04254108

Reaction notes

Loading…