2-CHLORO-N-[4-(4-CHLOROPHENYL)-1,3-THIAZOL-2-YL]ACETAMIDE synthesis
- Product Name:2-CHLORO-N-[4-(4-CHLOROPHENYL)-1,3-THIAZOL-2-YL]ACETAMIDE
- CAS Number:6125-31-1
- Molecular formula:C11H8Cl2N2OS
- Molecular Weight:287.17
2103-99-3
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$9.00/250mg
79-04-9
375 suppliers
$12.00/5g
6125-31-1
21 suppliers
$58.00/100mg
Yield:6125-31-1 100%
Reaction Conditions:
Stage #1: 4-(4-chlorophenyl)-2-thiazolaminewith triethylamine in dichloromethane at 0 - 5; for 0.5 h;
Stage #2: chloroacetyl chloride in dichloromethane at 0 - 20; for 2 h;
Steps:
The general procedure for the preparation of the known 2-(2-chloroacetamido)thiazoles (7) involved a modification of the procedure reported by Xu and collegues18.
General procedure: A solution of 2-amino-4-phenylthiazole 6a (0.530 g, 3 mmol) and Et3N (560 μL, 4 mmol) in dichloromethane (15 mL) was cooled to 0-5 C in an ice-bath and stirred for 30 min. 2-Chloroacetyl chloride (578 μL, 6.6 mmol) in dry dichloromethane (1.5 mL) was then added slowly, and the reaction mixture was allowed to warm to room temperature and stirred until the amine was completely consumed (ca. 1 h, as monitored by TLC). The reaction mixture was diluted with dichloromethane and washed successively with water and saturated brine. The organic layer was dried over anhydrous Na2SO4, the solvent was removed under reduced pressure and the residue was recrystallised from ethanol to give compound 7a (0.413 g, 54%) as light-grey crystals, mp 170-171 oC (Lit.18,20,26 171-173 oC). The remaining analogues were obtained similarly [7b (100%) as a brown solid, mp 194-195 oC (Lit.27 mp not cited); 7c (64%) as a brown solid, mp 241-243 oC (Lit.27 mp not cited); 7d (64%) as a brown solid, mp 135-137 oC (Lit.28 135 oC); 7e (0.262 g, 88%) as a yellow solid, mp 174-176 C (Lit.29 175 oC); 7f (70%) as a light-brown solid, mp 213-216 oC (Lit.30 216 oC).
References:
Olawode, Emmanuel O.;Tandlich, Roman;Prinsloo, Earl;Isaacs, Michelle;Hoppe, Heinrich;Seldon, Ronnett;Warner, Digby F.;Steenkamp, Vanessa;Kaye, Perry T. [Arkivoc,2018,vol. 2018,# 7,p. 110 - 118]
99-91-2
434 suppliers
$10.00/25g
6125-31-1
21 suppliers
$58.00/100mg
536-38-9
319 suppliers
$9.00/5g
6125-31-1
21 suppliers
$58.00/100mg
937-20-2
227 suppliers
$15.00/5G
6125-31-1
21 suppliers
$58.00/100mg