Sodium Hydroxide → HCID 178454819, compound

HRID 1957298Notes

Reaction equation

HRID 1957298 reaction equation
[OH-].[Na+].[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH2:41][C:42]([O:44]CC)=[S:43])([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]3[CH:40]=[CH:39][C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[N:32]=3)=[CH:25][CH:24]=2)[CH3:22])=[CH:17][CH:16]=1>O1CCOCC1.C(O)C>[N:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([CH2:41][C:42]([OH:44])=[S:43])([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:30][C:31]3[CH:40]=[CH:39][C:38]4[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=4)[N:32]=3)=[CH:27][CH:28]=2)[CH3:22])=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57207304HCID 57207304, compound

Product 1

HCID 178454819HCID 178454819, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

1N sodium hydroxide (0.5 mL) was added to a solution of ethyl 1,1-bis(4-(2-quinolylmethoxy)phenyl)eth-1-ylthioacetate from above in dioxane (10 mL) and ethanol (5 mL), and the resulting mixture was stirred at ambient temperature for 3 hours. The organics were removed in vacuo, the residue was diluted with water and acidified to pH 3. The solid was filtered, washed with water, dried under reduced pressure and recrystallized from methylene chloride-hexane to provide 170 mg of the title compound: mp 92°-94° C.; 1H NMR (300 MHz, DMSO-d6)δ 2.00 (s, 3 H), 3.32 (s, 2 H), 5.34 (s, 4 H), 7.02 (d, J=9 Hz, 4 H), 7.30 (d, J=9 Hz, 4 H), 7.63 (m, 4 H), 7.78 (m, 2 H), 8.00 (m, 4 H), 8.41 (d, J=8 Hz, 2 H); MS (DCI-NH3) m/z 587 (M+H)+. Anal. Calc'd. for C36H30N2O4S: C, 73.70; H, 5.15; N, 4.77. Found: C, 74.24; H, 5.28; N, 4.34.

Workup

  1. customThe organics were removed in vacuo
  2. additionthe residue was diluted with water
  3. filtrationThe solid was filtered
  4. washwashed with water
  5. customdried under reduced pressure
  6. customrecrystallized from methylene chloride-hexane

Sources & evidence

ORD record
ord-bd23fbea091c4e6687b5c8995fd5699d
Source dataset
uspto-grants-1998_07
Patent number
US05783586

Reaction notes

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