1,3-Dichloroacetone → 4-(chloromethyl)-2-(4-fluorophenyl)-1,3-thiazole

HRID 1397285Notes

Reaction equation

[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[S:7])=[CH:4][CH:3]=1.[Cl:11][CH2:12][C:13]([CH2:15]Cl)=O>>[Cl:11][CH2:12][C:13]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=2)[S:7][CH:15]=1

Participants

Reactant 2

HCID 107931,3-Dichloroacetone

HCID 7372234-Fluorothiobenzamide

Product 1

HCID 21108384-(chloromethyl)-2-(4-fluorophenyl)-1,3-thiazoleYield 89%

Procedure

This compound was synthesized from 4-fluorothiobenzamide and 1,3-dichloroacetone as described in example 39 step 1 (0.65 g, yield 89%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.96-7.93 (m, 2H), 7.30 (s, 1H), 7.16-7.12 (t, J=8.7 Hz, 2H), 4.75 (s, 2H). MS (ESI) m/z: Calculated for C10H7ClFNS: 227.00. found: 228.0 (M+H)+.

Sources & evidence

ORD record: ord-20f3c805806e41968fcc84d091d23051
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901156B2

Reaction notes

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