反应详情

温度

0 °C

To a solution of 1.95 g. (0.004 mol) of 4-amino-N-[4-(2,4-di-tert-pentylphenoxy)butyl]-1-hydroxy-2-naphthamide in 50 ml. of dry pyridine at 0° C., under nitrogen, was added 1.95 g. (0.004 mol) of 4-acetamido-8-(4-chlorosulfonylphenylazo)-5-hydroxy-1-naphthalenesulfonyl chloride. The solution was stirred at 0° C. for one hour, poured into 75 ml. of concentrated hydrochloric acid and 75 ml. of ice. The solid was collected on a filter funnel and dried. It was then chromatographed on a silica column, eluting with ethyl acetate to remove the product. The eluents were concentrated to dryness and the resulting solid reprecipitated from chloroform with hexane. The solid was collected on a filter funnel and dried to yield 1.1 g. (39%), m.p. 220°-2° C. dec. The 4-acetamido-8-(4-chlorosulfonylphenylazo)-5-hydroxy-1-naphthalenesulfonyl chloride was prepared by heating a solution of 9.7 g. (0.02 mol) of sodium 4-acetamido-5 -hydroxy-6-(4-sulfamoylphenylazo)-1-naphthalenesulfonate in 150 ml. of chlorosulfonic acid on a steam bath for ninety minutes. The solution was cooled and poured onto ice. The solid was collected on a filter funnel and dried to yield 9.4 g. (94%). The sodium 4-acetamido-5-hydroxy-8-(4-sulfamoylphenylazo)-1-naphthalenesulfonate was prepared as in Example 1.

1. additionpoured into 75 ml
2. customThe solid was collected on a filter funnel
3. customdried
4. customIt was then chromatographed on a silica column
5. washeluting with ethyl acetate
6. customto remove the product
7. concentrationThe eluents were concentrated to dryness
8. customthe resulting solid reprecipitated from chloroform with hexane
9. customThe solid was collected on a filter funnel
10. customdried
11. customto yield 1.1 g
12. temperatureby heating a solution of 9.7 g
13. temperatureThe solution was cooled
14. additionpoured onto ice
15. customThe solid was collected on a filter funnel
16. customdried
17. customto yield 9.4 g