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EXAMPLE 2 3,5-Diiodo-3'-Chloro-4'-(p-chlorophenoxy)-Salicylanilide A mixture of 31.0 g. of 4-amino-2,4'-dichlorobiphenyl ether, 47.4 g. of 3,5-diiodo salicylic acid, and 4.3 ml. of phosphorus trichloride in 235 ml. of chlorobenzene is refluxed for 3 hours. The hot solution is decanted from some insoluble residue and the crude product settles out of solution upon cooling to room temperature. Upon recrystallization from benzene, 27.8 g. of 3,5-diiodo-3'-chloro-4'-(p-chlorophenoxy)-salicylanilide, m.p. 168-170C. is obtained.
3
[ 22662-39-1 ]
3-[3-chloro-4-(4-chlorophenoxy)phenyl]-6,8-diiodo-2H-1,3-benzoxazine-2,4(3H)-dione[ No CAS ]
2-hydroxy-3,5-diiodobenzoic acid chloride[ No CAS ]
4-amino-2-chlorophenyl-p-chlorophenyl ether[ No CAS ]
[ 22662-39-1 ]
Yield
Reaction Conditions
Operation in experiment
92.1%
at 20 - 40℃; for 1h;
To the reaction vessel was added 28.4 g (0.1 mol) of 4-amino-2-chlorophenyl-p-chlorophenyl ether,(0.15 mol) of 3,5-diiodo-2-hydroxysalicyloyl chloride was slowly added dropwise at 20 C under stirring.After completion of the addition, the temperature was raised to 45 C and reacted for 3 hours. The dichloroethane was recovered by distillation under reduced pressure and the residue was added with purified water100ml, precipitation of white crystals, filtered, purified water washed once, dry, iodine sulfuric acid amide Salicylic acid 58.36g, HPLCThe purity was 98.79% and the yield was 92.10% (based on 4-amino-2-chlorophenyl-p-chlorophenyl ether).
3-(3-chloro-4-(4-chlorophenoxy)phenyl)-6,8-diiodobenzo[e][1,2,3]oxathiazin-4(3H)-one-2,2-dioxide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
56%
Triethylamine (85 muL, 0.61 mmol) was added to a solution of RAVEN [Compound 54] (256 mg, 0.40 mmol) in acetonitrile (1 mL) at room temperature.After stirring for 10 min, a solution of 1-(fluorosulfonyl)-2-3-dimethyl-1H-imidazole trifluoromethanesulfonate [Compound 4] (172 mg, 0.49 mmol) in acetonitrile (1 mL) was added to the system at one time. And react under argon for 1h, TLC (petroleum ether:Ethyl acetate = 10:1, product Rf = 0.57) followed by the reaction,Column chromatography (silica gel 300-400 mesh, petroleum ether:Ethyl acetate = 30:1) to give 3-(3-chloro-4-(4-chlorophenoxy)phenyl)-6-8diiodobenzene[e][1,2,3]oxine as a white solid Hethiazin-4(3H)-one-2,2-dioxide [Compound 55] (154 mg, 56%) (scheme 25).
Multi-step reaction with 3 steps
1.1: potassium hydroxide / 70 - 80 °C
1.2: 2.5 h / 110 - 120 °C
2.1: acetic acid; iron / ethanol; water / 2 h / Reflux
3.1: phosphorus trichloride / 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C
Multi-step reaction with 2 steps
1: acetic acid; iron / ethanol; water / 2 h / Reflux
2: phosphorus trichloride / 5,5-dimethyl-1,3-cyclohexadiene / 1.5 h / 110 °C