Hydrochloric Acid → HCID 135841572, compound

HRID 234580Notes

Reaction equation

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

Participants

Conditions

Temperature: 60 °C

Procedure

Then, in a 300 ml-reaction vessel, 10.4 g (2.42×10-2M) of 2-(6-acetoxy-2-naphthyl)-5-(4-hexylphenyl)-thiazole and 170 ml of 0.5N-solution of potassium hydroxide in ethanol, followed by stirring for 0.5 hour at 60° C. After cooling, the reaction mixture was poured into 400 ml of ice water and acidified with 6N-hydrochloric acid to precipitate a crystal. The crystal was recovered by filtration, washed with water and dissolved in ethanol, followed by treatment with activated carbon. The activated carbon was removed from the above mixture by filtration and the filtrate was condensed, followed by drying to provide a residue. The residue was recrystallized from ethanol to obtain 7.73 g of 2-(6-hydroxy-2-naphthyl)-5-(4-hexylphenyl)thiazole (Yield: 82.6%).

Workup

temperatureAfter cooling
customto precipitate a crystal
filtrationThe crystal was recovered by filtration
washwashed with water
dissolutiondissolved in ethanol
customThe activated carbon was removed from the above mixture by filtration
customcondensed
customby drying
customto provide a residue
customThe residue was recrystallized from ethanol

Sources & evidence

ORD record: ord-62b53e82f4fb4fdb8bbad40cc3f694b4
Source dataset: uspto-grants-1997_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05595685

Reaction notes

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