Bromomethyl 4-methoxyphenyl ketone → 2-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]acetonitrile

HRID 1397221Notes

Reaction equation

HRID 1397221 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=O.[C:13]([CH2:15][C:16]([NH2:18])=[S:17])#[N:14]>>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:18]=[C:16]([CH2:15][C:13]#[N:14])[S:17][CH:2]=2)=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 14162772-Cyanoethanethioamide

Product 1

HCID 23373102-[4-(4-methoxyphenyl)-1,3-thiazol-2-yl]acetonitrileYield 75%

Procedure

This compound was synthesized from 2-bromo-1-(4-methoxyphenyl)ethanone and 2-cyanothioacetamide as described in example 1 step 1 (1.5 g, yield 75%). 1H NMR (300 MHz, CDCl3) δ 7.83 (d, J=8.9 Hz, 2H), 7.35 (s, 1H), 6.98 (d, J=8.9 Hz, 2H), 4.17 (s, 2H), 3.86 (s, 3H). MS (ESI) m/z: Calculated for C12H10N2OS: 230.05. found: 231.2 (M+H)+.

Sources & evidence

ORD record
ord-be9e1db6d0124d6d9a24ccbbd2845a3d
Source dataset
uspto-grants-2014_12
Patent number
US08901156B2

Reaction notes

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