CN107698465A - 一种乙酰脲晶体化合物的合成方法 - Google Patents

一种乙酰脲晶体化合物的合成方法 Download PDF

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CN107698465A
CN107698465A CN201711124716.2A CN201711124716A CN107698465A CN 107698465 A CN107698465 A CN 107698465A CN 201711124716 A CN201711124716 A CN 201711124716A CN 107698465 A CN107698465 A CN 107698465A
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acetylurea
crystalline compounds
synthetic method
anhydrous
cell parameter
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CN107698465B (zh
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罗梅
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Hefei Xiangchen Chemical Engineering Co Ltd
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Hefei Xiangchen Chemical Engineering Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
    • C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
    • C07C273/1863—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety from urea

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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Abstract

一种乙酰脲晶体化合物的合成方法，包括合成、分离和纯化，所述的合成是无水无氧条件下，称取0.3370无水氯化锌，1‑苯基‑1，3‑丁二酮1.6449g及脲素1.9879g放入100mL两口烧瓶中，加入40mL氯苯回流搅拌；反应48小时后，得固体沉淀,再加入二氯甲烷、无水乙醇及DMF溶剂，并将溶液自然挥发，得无色透明色晶体,其化学式如下：

Description

一种乙酰脲晶体化合物的合成方法
一、技术领域
本发明涉及一种化合物及其制备方法，特别涉及一种含氮化合物及其制备方法，确切地说是一种乙酰脲二聚体晶体化合物的合成方法。
二、背景技术
乙酰脲化合物是重要的医药中间体，其合成方法及应用已有文献报道【1-3】
参考文献：
1.Acetylcarbamide complexes of some lanthanide bromides and chlorides：Syntheses and structures Alikberova，L.Yu.；Al′bov，D.V.；Bushmeleva，A.S.；Fedorova，G.A.；Kravchenko，V.V.， Russian Journal of Coordination Chemistry(2014)，40(12)，918-924.
2.New method of preparing N-acetylurea，Kurbanova，M.M.Izvestiya VysshikhUchebnykh Zavedenii，Khimiya i Khimicheskaya Tekhnologiya(2004)，47(8)，165.
3.Crystallographic characterization of monoacylated ureas，Hartung，Helmut；Lux，Georg； Hennicke，Rainer；Schellenberger，Alfred，Zeitschrift fuer Chemie(1973)，13(6)，234-235。
三、发明内容
本发明旨在为有机合成领域特别是制备药物提供一种高效催化剂所需的化合物配体，所要解决的技术问题是遴选相应的原料并建立相应的方法合成催化剂配体。
(一)本发明所称的化合物是以下化学式(I)所示的化合物：
其化学名称：乙酰脲。
该化合物(I)的合成方法是1，4-丁二酮与脲素在催化剂氯化锌及氯苯溶液中反应，该化学反应式如下：
本乙酰脲化合物(I)合成方法包括合成、分离和纯化，所述的合成是无水无氧条件下，
称取0.3370无水氯化锌，1-苯基-1，3-丁二酮1.6449g及脲素1.9879g放入100mL两口烧瓶中，加入40mL氯苯回流搅拌；反应48小时后，得固体沉淀，加入二氯甲烷、无水乙醇及 DMF溶剂，并将溶液自然挥发，得无色透明色晶体。
该反应的反应机理可推测为：
1-苯基-1，3-丁二酮与脲素在催化剂氯化锌的作用下酵素中的氨基与1，3丁二酮中的乙酰基发生和形成目标化合物I。
本乙酰脲晶体化合物(I)的制备，采用简易，高效的有机合成方法，一步合成，经X-衍射，NMR，IR及元素分析确定其结构。
图1是乙酰脲晶体化合物(1)的单晶衍射图。
四、具体实施方式
乙酰脲晶体化合物(I)的制备
称取0.3370无水氯化锌，1-苯基-1，3-丁二酮1.6449g及脲素1.9879g放入100mL两口烧瓶中，加入40mL氯苯回流搅拌：反应48小时后，得固体沉淀。加入二氯甲烷、无水乙醇及 DMF溶剂，并将溶液自然挥发，得无色透明色晶体，产率为85％，熔点234-236℃；元素分析数据C3H6N2O2，C：35.29％；H：5.92％；N：27.44％；实测值：C 35.05％；H： 5.84％；N：26.93％；HRMS(e/m)理论值：102.0429；实测值：102.0410；1HNMR(600MHz， CDCl3，27℃)，δ(ppm)＝10.10(s，1H)，7.96(s，1H)，6.67(s，1H)，2.00(s，3H)；红外光谱数据 (KBr，cm-1)：3379，3331，3226，1708，1670，1481，1417，1369，1253，1099，1032，941，811，700， 559，451；
氮化合物晶体数据如下：
经验式 C3H6N2O2
分子量 102.10
温度 300(2)K
波长
晶系，空间群 单斜晶系，P21/c
晶胞参数 α＝90°.
β＝98.739(5)°.
γ＝90°
体积 482.25(11)
电荷密度 4，1.406Mg/m^3
吸收校正参数 0.118mm^-1.
单胞内的电子数目 216
晶体大小 0.180x 0.150x 0.110mm
Theta角的范围 3.882to24.991
HKL的指标收集范围 -8＜＝h＜＝8，-6＜k＜＝6，-16＜l＜＝16
收集/独立衍射数据 8667/834[R(int)＝0.0334]
吸收校正的方法 多层扫描
精修使用的方法 F^2的矩阵最小二乘法
数据数目/使用限制的数目/参数数目 834/3/78
精修使用的方法 1.228
衍射点的一致性因子 R1＝0.0686，ωR2＝0.1672
可观察衍射的吻合因子 R1＝0.0706，ωR2＝0.1683
差值傅里叶图上的最大峰顶和峰谷 0.546and-0.311
晶体典型的键长数据：
晶体典型的键角数据：

Claims (1)

1.一种有如下晶胞参数的乙酰脲晶体化合物的合成方法，包括合成、分离和纯化，所述的合成是无水无氧条件下， 称取0.3370无水氯化锌，1-苯基-1，3-丁二酮1.6449g及脲素1.9879g放入100mL两口烧瓶中，加入40mL氯苯回流搅拌；反应48小时后，得固体沉淀, 再加入二氯甲烷、无水乙醇及DMF 溶剂，并将溶液自然挥发，得无色透明色晶体,其化学式如下：
（Ⅰ）
该乙酰脲晶体化合物（I）的晶胞参数：在273（2）k温度下，在牛津 X-射线单晶衍射仪上，用经石墨单色器单色化的单斜晶系,P21， 晶胞参数单斜晶系,P21/c； a = 7.0412(10) Åα = 90°； b = 5.0858(6) Å β = 98.739(5)°.；c = 13.5982(3) Å γ = 90 °。
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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110305043A (zh) * 2019-06-18 2019-10-08 合肥工业大学 一种缩二脲化合物的合成方法及用途
CN116375605A (zh) * 2023-02-28 2023-07-04 山东聊城鲁西硝基复肥有限公司 一种连续化n-甲酸基脲的生产工艺

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107253923A (zh) * 2017-08-07 2017-10-17 合肥祥晨化工有限公司 一种乙酰脲二聚体晶体化合物的合成方法及用途
CN107337617A (zh) * 2017-08-07 2017-11-10 合肥祥晨化工有限公司 一种乙酰脲内聚体晶体化合物的合成方法及用途

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107253923A (zh) * 2017-08-07 2017-10-17 合肥祥晨化工有限公司 一种乙酰脲二聚体晶体化合物的合成方法及用途
CN107337617A (zh) * 2017-08-07 2017-11-10 合肥祥晨化工有限公司 一种乙酰脲内聚体晶体化合物的合成方法及用途

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110305043A (zh) * 2019-06-18 2019-10-08 合肥工业大学 一种缩二脲化合物的合成方法及用途
CN116375605A (zh) * 2023-02-28 2023-07-04 山东聊城鲁西硝基复肥有限公司 一种连续化n-甲酸基脲的生产工艺
CN116375605B (zh) * 2023-02-28 2024-04-19 山东聊城鲁西硝基复肥有限公司 一种连续化n-甲酸基脲的生产工艺

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