تفاعل #1340586

معادلة التفاعل

2,6-dibromo-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)-phenylamine

3-nitro-4-(1H-1,2,4-triazol-1-yl)benzoic acid

3-nitro-4-(1H-1,2,4-triazol-1-yl)benzoic acid

triethylamine

triethylamine

→

N-[2,6-dibromo-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)phenyl]-3-nitro-4-(1,2,4-triazol-1-yl)benzamide

المردود 65.0%

المذيبات

1,2-dichloroethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةat reflux for 16 hours
2. 2
   workup.ADDITIONwere added over the course of 48 hours
3. 3
   أخرىThe reaction was quenched by addition of aqueous hydrochloric acid (1M)
4. 4
   أخرىthe phases were separated
5. 5
   غسيلThe organic phase was washed with saturated aqueous sodium hydrogen carbonate
6. 6
   تجفيفdried over sodium sulfate
7. 7
   تركيزconcentrated
8. 8
   أخرىThe residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:2)
9. 9
   أخرىto give Compound No

الإجراء التجريبي

To a suspension of 2,6-dibromo-4-(1,2,2,3,3,3-hexafluoro-1-trifluoromethylpropyl)-phenylamine (Example I1) (635 mg, 1.35 mmol) in 1,2-dichloroethane (6.5 ml) was added triethylamine (0.57 ml, 4.06 mmol), followed by 3-nitro-4-(1H-1,2,4-triazol-1-yl)benzoic acid (634 mg, 2.7 mmol) and bis(2-oxo-3-oxazolidinyl)phosphonic chloride (“BOP—Cl”) (689 mg, 2.7 mmol). The reaction mixture was stirred at reflux for 16 hours. The progress of the reaction was followed by thin layer chromatography and, because it was necessary in this case, further doses of 3-nitro-4-(1H-1,2,4-triazol-1-yl)benzoic acid (4×0.675 mmol), bis(2-oxo-3-oxazolidinyl)phosphonic chloride (4×1.35 mmol) and triethylamine (4×1.35 mmol) were added over the course of 48 hours. The reaction was quenched by addition of aqueous hydrochloric acid (1M) and the phases were separated. The organic phase was washed with saturated aqueous sodium hydrogen carbonate, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (eluent: cyclohexane/ethyl acetate 1:2) to give Compound No. A4 of Table A (605 mg, 65% yield).

المصدر