2-Naphthalenethiol → HCID 18668987, compound

HRID 1058671Notes

Reaction equation

[OH-].[Na+].[CH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][C:4]=1[SH:13].F[C:15]1[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][C:16]=1[CH:17]=[O:18]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>[CH:17]([C:16]1[CH:19]=[C:20]([N+:23]([O-:25])=[O:24])[CH:21]=[CH:22][C:15]=1[S:13][C:4]1[CH:5]=[CH:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:3]=1)=[O:18]

Participants

Conditions

Temperature: 25 °C

Procedure

A 2.5 mol/L sodium hydroxide aqueous solution (2.1 mL, 5.2 mmol) and tetrabutylammonium bromide (0.020 g, 0.061 mmol) were added to 2-naphthalenethiol (0.20 g, 1.2 mmol), followed by stirring at 25° C. for 15 minutes. A toluene (2.1 mL) solution of 2-fluoro-5-nitrobenzaldehyde (0.21 g, 1.2 mmol) was added to the reaction liquid, followed by stirring at 110° C. for 3.5 hours. The conventional post-reaction treatment was performed to give 2-[(2-formyl-4-nitrophenyl)thio]naphthalene. 2-[(2-Formyl-4-nitrophenyl)thio]naphthalene (0.30 g, 0.98 mmol) was dissolved in toluene (15 mL), and 2,4-thiazolidinedione (0.46 g, 3.9 mmol), piperidine (0.039 mL, 0.39 mmol), acetic acid (0.022 mL, 0.039 mmol) and molecular sieves 4A (1.5 g) were added thereto, followed by stirring at 110° C. for 2.5 hours. After the conventional post-reaction treatment, the product was triturated with ethanol to give Compound 171 (0.13 g, yield 33%).

Workup

stirringby stirring at 110° C. for 3.5 hours

Sources & evidence

ORD record: ord-dd83a2e2a84c4cf29cc60cc498445b75
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518268B1

Reaction notes

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