2-Chloro-1-(1,2,3,4-tetrahydroquinolin-1-yl)ethan-1-one → 1-(3,4-dihydro-2H-quinolin-1-yl)-2-[(4,5-diphenyl-1,3-oxazol-2-yl)sulfanyl]ethanone

HRID 1404913Notes

Reaction equation

HRID 1404913 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]1([C:21]2[N:22]=[C:23]([SH:32])[O:24][C:25]=2[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>>[N:5]1([C:3](=[O:4])[CH2:2][S:32][C:23]2[O:24][C:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[C:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=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 178527826HCID 178527826, compound

Product 1

HCID 34480971-(3,4-dihydro-2H-quinolin-1-yl)-2-[(4,5-diphenyl-1,3-oxazol-2-yl)sulfanyl]ethanoneYield 40%

Procedure

The title compound was synthesized according to General Procedure A using compound 4 as the electrophile and 4,5-diphenyloxazole-2-thiol as the nucleophile to yield 20 as an off-white solid (40%): MS m/z: 427 (M+H)+. Anal. Calcd. For, C26H22N2O2S: C, 73.21; H, 5.20; N, 6.57; S, 7.52. Found: C, 73.49; H, 5.13; N, 6.57; S, 7.42.

Workup

  1. customThe title compound was synthesized

Sources & evidence

ORD record
ord-85c60151de8349728915098b5f6c096e
Source dataset
uspto-grants-2014_12
Patent number
US08916550B2

Reaction notes

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