반응 #344426

반응 방정식

N1 -(2,2,2,-trifluoroethyl)-2-nitro-p-phenylene-diamine

1 -(2,2,2-trifluoroethyl)-2-nitro-p-phenylenediamine

2-chloroethyl chloroformate

hexane

→

2-chloroethyl-N-[4-(2,2,2-trifluoroethyl)-3-nitrophenyl]-carbamate

용매

dioxane

반응 조건

후처리

1. 1
   여과filtered
2. 2
   세척washed with ethyl acetate
3. 3
   세척The combined filtrate was washed with water and brine
4. 4
   건조dried (Na2SO4)
5. 5
   기타evaporated
6. 6
   기타to give a brown oil

실험 절차

A mixture of N1 -(2,2,2,-trifluoroethyl)-2-nitro-p-phenylene-diamine (6) (0.705 g, 3 mmol), 2-chloroethyl chloroformate (0.515 g, 3.6 mmol) and CaCo3 (0.40 g, 4 mmol) in dioxane (10 ml) was stirred at 80° C. for 20 minutes, filtered and washed with ethyl acetate. The combined filtrate was washed with water and brine, dried (Na2SO4), and evaporated to give a brown oil. Trituration with hexane gave 2-chloroethyl-N-[4-(2,2,2-trifluoroethyl)-3-nitrophenyl]-carbamate (8) as an orange solid. The unpurified carbamate (8) was dissolved in aqueous ethanol (ETOH: H2O, 15/5 ml) and powdered KOH (1.35 g) was added. The mixture was stirred at 90° C. for 20 minutes and then poured onto crushed ice (20 g) . The resultant mixture was extracted with ethyl acetate, washed with water and brine, dried (Na2SO4), and evaporated to give 0.544 g (65% yield) of N1 -(2,2,2-trifluoroethyl)-N4 -(2-hydroxyethyl)-2-nitro-p-phenylenediamine (9): mp 93°-95° C.; MS m/e 279(M+); 1HNMR (acetone-d6), δ3.25 (m, 2H), 3.76 (m, 2H), 3.91 (bs, 1H), 4.34 (m, 2H), 4.98 (bs, 1H), 7.19 (m, 2H), 7.35 (s,1H), 7.80 (bs, 1H).

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