반응 #423613

반응 방정식

acid 2-2

Methyl 4,6-dichloro-3-methoxy-2-nitrobenzoate

propylamine

→

amide

수율 92.0%

4,6-Dichloro-3-methoxy-N-propyl-2-nitrobenzamide

수율 92.0%

용매

thionyl chloride

반응 조건

후처리

1. 1
   온도After cooling
2. 2
   기타the volatiles were removed in vacuo
3. 3
   기타the residue was azeotroped with toluene
4. 4
   건조The resulting acid chloride was dried at high vacuum
5. 5
   workup.DISSOLUTIONdissolved in anhydrous CH2Cl2 (50 mL)
6. 6
   온도The reaction was warmed to room temperature for 2 h
7. 7
   기타The solvent was removed in vacuo
8. 8
   추출The aqueous layer was extracted three times into EtOAc
9. 9
   세척the combined organic layers were washed with H2O
10. 10
    건조dried over Na2SO4
11. 11
    여과filtered
12. 12
    농축concentrated

실험 절차

The acid 2-2 (1.41 g, 5.3 mmol) was heated to reflux in thionyl chloride (20 mL) for 2 h. After cooling, the volatiles were removed in vacuo and the residue was azeotroped with toluene. The resulting acid chloride was dried at high vacuum and then dissolved in anhydrous CH2Cl2 (50 mL), cooled to 0° C. then treated with propylamine (2.45 mL, 29.9 mmol). The reaction was warmed to room temperature for 2 h. The solvent was removed in vacuo and the residue was taken up in EtOAc and brine. The aqueous layer was extracted three times into EtOAc and the combined organic layers were washed with H2O, dried over Na2SO4, filtered and concentrated to provide the amide in which R is propyl 4-5 as a light orange solid. (1.5 g, 92% yield). 1H NMR (400 MHz, d6-DMSO) δ 0.91 (t, J=7.0 Hz, 3H), 1.40 (q, J=7.0 Hz, 2H), 3.07 (q, J=7.0 Hz, 2H), 3.84 (s, 3H), 8.13 (s, 1H), 8.84 (br s, 1H).

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