问题：合成N-碘代丁二酰亚胺
类型：求助 (悬赏分:3分)
提问：pingyamin
等级：▲▲
版块：有机化学问题(jimuwei,fpcwin1211,netpanda,yjgzfl,Ftian,)
信誉：93%
回复：12
阅读：973
时间：2009-02-18 12:09:07 编辑加入/取消收藏订制/取消短消息举报该贴

由N-羟基丁二酰亚胺合成N-碘代丁二酰亚胺有没有方法 ----不经过卤交换直接碘代的

回复人：pingyamin,▲▲ (Go Ahead!!) 时间：2009-02-18 21:08:54 编辑	1楼
Claymore 把你文献借我看看嘿嘿

回复人：合成小象,★ (...您看到的是神奇的生命现象，我看到的是规律的有机反应...) 时间：2009-02-18 12:31:09 编辑	2楼
哥们，这个东西跟NBS一样，有卖的，叫做NIS。直接买就好了。 B 溴 I 碘

回复人：pingyamin,▲▲ (Go Ahead!!) 时间：2009-02-18 12:47:33 编辑	3楼
我知道有卖的我想做来卖啊

回复人：claymore,★★★★★ (C-H活化，kumada,suzuki,stille,negishi.cross-coupling.) 时间：2009-02-18 14:03:11 编辑	4楼
丁二酸与羟基胺环合成丁二酰亚胺，再1，4-二氧六环做溶剂，碘代

回复人：pingyamin,▲▲ (Go Ahead!!) 时间：2009-02-18 14:42:19 编辑	5楼
碘代是直接用单质碘还是用其他试剂 NaI？碘代有没有相关文献？

回复人：claymore,★★★★★ (C-H活化，kumada,suzuki,stille,negishi.cross-coupling.) 时间：2009-02-18 15:29:05 编辑	6楼
N-Iodosuccinimide还不如直接买

回复人：claymore,★★★★★ (C-H活化，kumada,suzuki,stille,negishi.cross-coupling.) 时间：2009-02-18 15:36:21 编辑

7楼

Twenty grams (0.079 mole) of iodine and 90 ml. of dried dioxane (Note 1) are placed in a widemouthed,
screw-cap, brown bottle of 150–200 ml. capacity. Most of the iodine dissolves. Eighteen
grams (0.087 mole) of thoroughly dried N-silver succinimide (Note 2) is added, and the bottle is shaken
vigorously for several minutes. The mixture is occasionally shaken in the course of an hour and then is
warmed in a water bath at 50° for 5 minutes. It is now filtered hot through a Büchner funnel into a 500-
ml. filter flask well wrapped with black paper or aluminum foil. The silver iodide that is collected is
washed with a 10-ml. portion of warm dioxane. Carbon tetrachloride (200 ml.) is added to the combined
filtrates in the filter flask, and the solution is chilled overnight at −8° to −20°. N-Iodosuccinimide
separates as colorless crystals. It is collected on a Büchner funnel with as little exposure to light as
possible, washed with 25 ml. of carbon tetrachloride, and dried with suction. After being dried overnight
in the dark at 25° (1 mm.) the N-iodosuccinimide weighs 14.3–15.1 g. (81–85% yield) and melts with
decomposition at 193–199° (Note 3).

回复人：claymore,★★★★★ (C-H活化，kumada,suzuki,stille,negishi.cross-coupling.) 时间：2009-02-18 15:36:43 编辑

8楼

1. The dioxane is purified only by the use of sodium strips and distillation.3 The checkers used a newly
opened bottle of "Spectroquality Reagent" dioxane (Matheson, Coleman and Bell) without further
treatment.
2. N-Silver succinimide was prepared by the method of Djerassi and Lenk.4 The checkers rapidly added
a solution of 64 g. (1.6 moles) of sodium hydroxide in 300 ml. of water dropwise to a stirred solution of
249 g. (1.47 moles) of silver nitrate in 700 ml. of water at room temperature. The silver oxide that
formed was separated on a Büchner funnel and washed with water. The moist oxide was added in one
portion to a boiling solution of 133 g. (1.34 moles) of succinimide in 4 l. of water. The reaction vessel
was wrapped with aluminum foil in order to exclude as much light as possible. After 45 minutes, the
suspension was filtered through a heated Büchner funnel into a filter flask also wrapped with aluminum
foil. The filtrate was allowed to stand at room temperature overnight, during which time N-silver
succinimide crystallized. The N-silver succinimide was separated on a Büchner funnel, dried in air
under suction, and ground to a powder. After being dried in a vacuum oven for 1 hour at 110°, it
weighed 128 g. (47%). N-Silver succinimide should be stored in a brown bottle.
3. This material is pure enough to use in the preparation of α-iodoketones. The checkers found that, after
one recrystallization from a mixture of dioxane and carbon tetrachloride, the N-iodosuccinimide melted
with decomposition at 195–200°. Pure N-iodosuccinimide is reported to melt at 200–201°.4

回复人：claymore,★★★★★ (C-H活化，kumada,suzuki,stille,negishi.cross-coupling.) 时间：2009-02-18 15:36:55 编辑	9楼
N-Iodosuccinimide has been prepared by the action of iodine on N-silver succinimide,4,5 and by the action of iodine monochloride on the sodium salt of succinimide.6 The present procedure is essentially that of Djerassi and Lenk,4 with the modification that dioxane is the reaction medium instead of acetone; dioxane gives a better yield without formation of a lachrymatory by-product.

回复人：claymore,★★★★★ (C-H活化，kumada,suzuki,stille,negishi.cross-coupling.) 时间：2009-02-18 15:37:09 编辑

10楼

Appendix
Chemical Abstracts Nomenclature (Collective Index Number);
(Registry Number)
N-silver succinimide
sodium hydroxide (1310-73-2)
silver oxide (20667-12-3)
silver nitrate (7761-88-8)
carbon tetrachloride (56-23-5)
iodine (7553-56-2)
acetone (67-64-1)
sodium (13966-32-0)
Succinimide (123-56-8)
dioxane (5703-46-8)
iodine monochloride (7790-99-0)
N-bromosuccinimide (128-08-5)
fluorenone (486-25-9)
silver iodide (7783-96-2)
N-Iodosuccinimide,
Succinimide, N-iodo- (516-12-1)
sodium salt of succinimide
Copyright © 1921-2005, Organic Syntheses, Inc. All Rights Reserved

得分人：claymore :3,

问题讨论没有结束...

您尚未进入本论坛,登录之后才可以回贴

6msec