1,3-Dichloroacetone → 4-(Chloromethyl)-2-(4-methoxyphenyl)-1,3-oxazole

HRID 1397415Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[CH:5][CH:4]=1.[Cl:12][CH2:13][C:14]([CH2:16]Cl)=O>>[Cl:12][CH2:13][C:14]1[N:9]=[C:7]([C:6]2[CH:10]=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[O:8][CH:16]=1

Participants

Reactant 2

HCID 107931,3-Dichloroacetone

HCID 769594-Methoxybenzamide

Product 1

HCID 199587944-(Chloromethyl)-2-(4-methoxyphenyl)-1,3-oxazoleYield 78%

Procedure

This compound was synthesized from 4-methoxybenzamide and 1,3-dichloroacetone as described in example 74 step 1 (2.3 g, yield 78%) as a yellow solid. 1H NMR (400 MHz, CDCl3) δ 7.98-7.96 (d, J=8.3 Hz, 2H), 7.65 (s, 1H), 6.97-6.95 (d, J=8.3 Hz, 2H), 4.56 (s, 2H), 3.86 (s, 3H). MS (ESI) m/z: Calculated for C11H10ClNO2: 223.04. found: 223.8 (M+H)+.

Sources & evidence

ORD record: ord-dc5132472e8a45849994176d9e5487cd
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901156B2

Reaction notes

Loading…