Hydrochloric Acid → 2-Hexyl-5-(6-hydroxynaphthalene-2-yl)-1,3,4-thiadiazole

HRID 1534767Notes

Reaction equation

HRID 1534767 reaction equation
[OH-].[K+].[CH2:3]([C:9]1[S:10][C:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([O:24]C(=O)C)[CH:20]=3)[CH:15]=2)=[N:12][N:13]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].O.Cl>C(O)C>[CH2:3]([C:9]1[S:10][C:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[C:19]([OH:24])[CH:20]=3)[CH:15]=2)=[N:12][N:13]=1)[CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14797Potassium HydroxideHCID 199079422-Hexyl-5-(6-acetoxynaphthalene-2-yl)-1,3,4-thiadiazole

Product 1

HCID 1360772002-Hexyl-5-(6-hydroxynaphthalene-2-yl)-1,3,4-thiadiazoleYield 74.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.50 g (22.7 mM) of potassium hydroxide was dissolved in 72 ml of ethanol at 60°-65° C. To the solution, 2.90 g (8.18 mM) of 2-hexyl-5-(6-acetoxynaphthalene-2-yl)-1,3,4-thiadiazole was added, followed by stirring for 20 minutes at 60°-65° C. The reaction mixture was poured into 200 ml of iced water and 3 ml of concentrated hydrochloric acid was added thereto to precipitate a crystal. The crystal was recovered by filtration and washed with water to obtain 1.90 g of 2-hexyl-5-(6-hydroxynaphthalene-2-yl)-1,3,4-thiadiazole (Yield: 71.9 %). ##STR138##

Workup

  1. additionwas added
  2. customto precipitate a crystal
  3. filtrationThe crystal was recovered by filtration
  4. washwashed with water

Sources & evidence

ORD record
ord-024ae5efd6834466b85091b87e28a033
Source dataset
uspto-grants-1992_02
Patent number
US05091109

Reaction notes

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