2-Chloro-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-one → 2-[2-(3,4-Dihydro-2H-quinolin-1-yl)-2-oxo-ethylsulfanyl]-benzothiazol-5-carbonitrile

HRID 1404922Notes

Reaction equation

HRID 1404922 reaction equation
Cl[CH2:2][C:3]([N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1)=[O:4].[C:15]([C:17]1[CH:18]=[CH:19][C:20]2[S:24][C:23]([SH:25])=[N:22][C:21]=2[CH:26]=1)#[N:16]>>[N:5]1([C:3](=[O:4])[CH2:2][S:25][C:23]2[S:24][C:20]3[CH:19]=[CH:18][C:17]([C:15]#[N:16])=[CH:26][C:21]=3[N:22]=2)[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][CH2:6]1

Participants

3

Reactant 2

HCID 2401372-Chloro-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-oneHCID 178509540HCID 178509540, compound

Product 1

HCID 685138512-[2-(3,4-Dihydro-2H-quinolin-1-yl)-2-oxo-ethylsulfanyl]-benzothiazol-5-carbonitrileYield 74%

Procedure

The title compound was synthesized according to General Procedure A using compound 4 as the electrophile and 2-mercaptobenzo[d]thiazole-5-carbonitrile (14) as the nucleophile to yield 32 as a white solid (74%): MS m/z: 366 (M+H)+. Anal. Calcd. For, C19H15N3OS2: C, 62.44; H, 4.14; N, 11.50; S, 17.55. Found: C, 62.47; H, 4.36; N, 11.35; S, 17.65.

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-e3c21939725f4883833e7bfae325b190
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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