1-Naphthalenethiol → 1-[5-(Naphth-1-ylsulfanyl)-4-nitro-2-thienyl]ethanone

HRID 1192031Notes

Reaction equation

HRID 1192031 reaction equation
[C:1]1([SH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.Cl[C:13]1[S:17][C:16]([C:18](=[O:20])[CH3:19])=[CH:15][C:14]=1[N+:21]([O-:23])=[O:22]>>[C:1]1([S:11][C:13]2[S:17][C:16]([C:18](=[O:20])[CH3:19])=[CH:15][C:14]=2[N+:21]([O-:23])=[O:22])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 682591-NaphthalenethiolHCID 5211051-(5-Chloro-4-nitrothiophen-2-yl)ethan-1-one

Product 1

HCID 469319551-[5-(Naphth-1-ylsulfanyl)-4-nitro-2-thienyl]ethanoneYield 29.1%

Procedure

Prepared according to the procedure described as in Step B for example 1 from 1-naphthalenethiol (320 mg, 2 mmol) and 1-(5-Chloro-4-nitro-2-thienyl)ethanone (412 mg, 2 mmol) to afforded the title compound as a yellow solid (192 mg, 29% yield). 1H NMR (300 MHz, CDCl3) δ: 8.33 (1H, m), 8.11 (1H, m), 8.08 (1H, s), 7.98 (2H, m), 7.59 (3H, m), 2.43 (3H, s).

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-4749d08c67c74944be380697b0ed69ce
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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