CN115108930A - 一种氮苯基苯甲酰胺化合物的合成方法及用途 - Google Patents
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- -1 aminophenyl benzamide compound Chemical class 0.000 title claims abstract description 8
- 238000010189 synthetic method Methods 0.000 title abstract description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims abstract description 27
- 239000013078 crystal Substances 0.000 claims abstract description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims abstract description 10
- 238000006243 chemical reaction Methods 0.000 claims abstract description 9
- 238000004440 column chromatography Methods 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 239000002904 solvent Substances 0.000 claims abstract description 7
- 229910052763 palladium Inorganic materials 0.000 claims abstract description 6
- DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 claims abstract description 5
- 239000003208 petroleum Substances 0.000 claims abstract description 5
- 238000003756 stirring Methods 0.000 claims abstract description 5
- SXZIXHOMFPUIRK-UHFFFAOYSA-N diphenylmethanimine Chemical compound C=1C=CC=CC=1C(=N)C1=CC=CC=C1 SXZIXHOMFPUIRK-UHFFFAOYSA-N 0.000 claims abstract description 4
- 230000003197 catalytic effect Effects 0.000 claims abstract description 3
- 150000002825 nitriles Chemical class 0.000 claims abstract description 3
- 239000003054 catalyst Substances 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 6
- 238000002447 crystallographic data Methods 0.000 claims description 2
- FIQOGXOIIDJKJL-UHFFFAOYSA-N 3-nitro-2-phenylbenzamide Chemical compound NC(=O)C1=CC=CC([N+]([O-])=O)=C1C1=CC=CC=C1 FIQOGXOIIDJKJL-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910002804 graphite Inorganic materials 0.000 claims 1
- 239000010439 graphite Substances 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 4
- 238000000926 separation method Methods 0.000 abstract description 3
- 238000005303 weighing Methods 0.000 abstract description 3
- 239000000463 material Substances 0.000 abstract description 2
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 abstract 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- XRAPKIOOHSMBKO-UHFFFAOYSA-N 3-amino-2-phenylbenzamide Chemical compound NC(=O)C1=CC=CC(N)=C1C1=CC=CC=C1 XRAPKIOOHSMBKO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- STVVMTBJNDTZBF-SECBINFHSA-N (2r)-2-amino-3-phenylpropan-1-ol Chemical compound OC[C@H](N)CC1=CC=CC=C1 STVVMTBJNDTZBF-SECBINFHSA-N 0.000 description 1
- 238000004009 13C{1H}-NMR spectroscopy Methods 0.000 description 1
- ZFOCMWZKYXXLBD-UHFFFAOYSA-N 2,4-dimethylfuro[3,2-c]quinoline Chemical compound C1=CC=CC2=C(OC(C)=C3)C3=C(C)N=C21 ZFOCMWZKYXXLBD-UHFFFAOYSA-N 0.000 description 1
- 238000006237 Beckmann rearrangement reaction Methods 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 1
- BHXFKXOIODIUJO-UHFFFAOYSA-N benzene-1,4-dicarbonitrile Chemical compound N#CC1=CC=C(C#N)C=C1 BHXFKXOIODIUJO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical class BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000006880 cross-coupling reaction Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 238000006459 hydrosilylation reaction Methods 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- DJWUNCQRNNEAKC-UHFFFAOYSA-L zinc acetate Chemical class [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
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- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
- B01J31/02—Catalysts comprising hydrides, coordination complexes or organic compounds containing organic compounds or metal hydrides
- B01J31/0234—Nitrogen-, phosphorus-, arsenic- or antimony-containing compounds
- B01J31/0235—Nitrogen containing compounds
- B01J31/0245—Nitrogen containing compounds being derivatives of carboxylic or carbonic acids
- B01J31/0247—Imides, amides or imidates (R-C=NR(OR))
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
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- B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
- B01J2231/40—Substitution reactions at carbon centres, e.g. C-C or C-X, i.e. carbon-hetero atom, cross-coupling, C-H activation or ring-opening reactions
- B01J2231/42—Catalytic cross-coupling, i.e. connection of previously not connected C-atoms or C- and X-atoms without rearrangement
- B01J2231/4205—C-C cross-coupling, e.g. metal catalyzed or Friedel-Crafts type
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Abstract
一种氮苯基苯甲酰胺化合物，其化学式如下：
该晶体化合物(I)的合成方法是无水无氧条件下，称取二苯甲酮肟0.0235g及0.0197g三甲基硅腈和钯配合物0.1147g，放入25.0mL烧瓶中，加入2.0mL二氯甲烷做溶剂，室温搅拌48小时后，柱层析分离，用石油醚/二氯甲烷(3/7)洗脱，将收集的第一组分点自然挥发，柱层析后得氮苯基苯甲酰胺晶体。4.由权利要求1所述的晶体化合物(I)的用途，是作为催化剂在二苯甲酮亚胺的腈硅化反应中显示了较好的催化性能，其转化率高达99％。
Description
一、技术领域
本发明涉及一种化合物的用途，特别涉及一种含氮化合物的用途，确切地说是一种氮苯基苯甲酰胺化合物。
二、背景技术
氮苯基苯甲酰胺化合物是重要的医药中间体，其用途极为广泛。其合成方法及应用已有大量文献报道【1-3】。
参考文献：
1.Journal of the American Chemical Society，Beckmann rearrangements.Anew method，195274，2680-1.
2.Synthesis of dibromo ketones by the reaction of the environmentallybenign H2O2-HBr system with oximes,Terent'ev,Alexander O.；Central EuropeanJournal of Chemistry(2012),10(2),360-367
3.Enantioselective Hydrosilylation of Imines Catalyzed by Chiral ZincAcetate Complexes Bezlada,Agata；Journal of Organic Chemistry(2016),81(1),336-342
4.Nitrimines as Reagents for Metal-Free Formal C(sp2)-C(sp2)Cross-Coupling Reactions Angeles-Dunham,Veronica V.；Angewandte Chemie,InternationalEdition(2014),53(52),14538-14541
三、发明内容
(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：氮苯基苯甲酰胺
本化合物(I)的合成方法是称取二苯甲酮肟0.0235g及0.0197g三甲基硅腈和钯配合物0.1147g，放入5.0mL烧瓶中，加入2.0mL二氯甲烷做溶剂，室温搅拌48小时后，柱层析分离，用石油醚/二氯甲烷(3/7)洗脱，将收集的第一组分点自然挥发，柱层析后得氮苯基苯甲酰胺晶体。
该反应的反应机理可推测如下：二苯甲酮肟在钯配合物作用下，首先，与三甲基硅腈作用
四、附图说明
图1氮苯基苯甲酰胺的单晶衍射图。
五、具体实施方式
1.手性钯配合物的制备
(1)[1,4-(4R)-二苄基－2－噁唑啉基]苯的制备
在100mL两口瓶中,无水无氧条件下,加入无水ZnCl21.54g(10.64mmol),40ml氯苯,1,4-二氰基苯5.62g(39.2mmol),D-苯丙氨醇18.8g,将混合物在高温下回流60h,停止反应,减压以除去溶剂,,将剩余物用水溶解,并用CHCl3(20mLx2)萃取,有机相用无水硫酸钠干燥,旋转除去溶剂,将粗产品用石油醚/二氯甲烷(4:1)柱层析,得浅绿色粘稠状液体,产率52％；白色晶体,熔点:48-50℃；[α]25 D＝+39.1°(c 0.098,CHCl3)；1HNMR(500MHz,298K,CDCl3)δppm 7.98(s,4H),7.22-7.32(m,10H,ArH),4.59-4.61(m,2H,CH×2),4.37(t,J＝8.9Hz,2H,CH×2),4.16(t,J＝7.9Hz,2H,CH×2),3.23,3.26(dd,J＝5.1,5.1Hz,2H,CH×2),2.71,2.75(dd,J＝9.0,9.0Hz,2H,CH2×2)；13C{1H}NMR(125MHz,298K,CDCl3)163.4,137.8,130.2,129.2,128.6,128.2,126.6,72.0,68.0,41.8；HRMS(EI)m/z(％)calcd forC26H24N2O2396.1838；found 396.1833.νmax(cm-1)3420,3081,3054,3031,2988,2956,2893,2231,1647,1608,1497,1454,1406,1359,1343,1317,1293,1276,1262,1201,1174,1073,1046,1017,967,953,860,840,755,697,669,548,527；
双{[1,4-(4R)-二苄基－2－噁唑啉基苯]氯化钯}配合物的制备100mL两口瓶中,无水无氧条件下,加入氯化钯1.7000g(4.92mmol),1,4-(4R)-二苄基－2－噁唑啉基苯1.4283g，氯苯100mL将混合物在高温下回流48h,停止反应,减压以除去溶剂,,将剩余物三氯甲烷及乙醇溶解，自然挥发，得红褐色配合物得晶体，产率：95％；m.p.:>200℃,[a]5 D＝+16.44°(c 0.0076,CH3OH)；1H NMR(600MHz,CDCl3),δppm 9.2(s,8H,ArH),7.26-7.44(m,20H，ArH)),4.91-4.93(m,4H),4.67-4.73(m，8H),3.85-3.86(m,4H),3.23-3.27(m,4H)；13CNMR(150MHz,CDCl3)δppm 165.9(x4),136.5(x4),130.3(x6),129.3(x6),129.2(x6),129.1(x4),127.3(x4),72.9(x4),68.8(x4),67.0(x4),41.5(x4)；νmax(cm-1)3459,3063,3042,3027,3002,2945,2934,2921,2851,1648,1633,1607,1566,1507,1494,1474,1454,1439,1417,1369,1302,1282,1246,1289,2957,2929,2872,1642,1609,1572,1509,1480,1464,1416,1379,1331,1288,1246,1241,1205,1179,1154,1050,1029,1021,970,938,918,903,855,845,762,682,633,601,588,528；Elemental analysis for C52H48N4Cl4O4Pd2,found C53.90％,H：4.353％；N:4.68％；requires C 54.42％,H 4.22％,N 4.88％；ESI(C52H48N4Cl4O4Pd2·H2O)Calcd:1165.6350；found:1166.0574
2.氮苯基苯甲酰胺的制备
无水无氧条件下，称取二苯甲酮肟0.0235g及0.0197g三甲基硅腈和钯配合物0.1147g，放入5.0mL烧瓶中，加入2.0mL二氯甲烷做溶剂，室温搅拌48小时后，柱层析分离，用石油醚/二氯甲烷(3/7)洗脱，将收集的第一组分点自然挥发，柱层析后得氮苯基苯甲酰胺晶体。m.p.99-102℃；1HNMR(500MHz,CDCl3,27℃),δ(ppm)＝7.86-7.88(m,2H),7.65(d,J＝7.9Hz，2H),7.48-7.56(m，3H),7.26-7.40(m,1H)；13CNMR(125MHz,CDCl3,27℃)165.7,137.9，135.0,131.9,129.1,128.8，127.0,120.2；IR(KBr):3342,1654，1599，1526，1491，1448，1437，1321，1260，1178，1075，10278，928，910，885，791，748，7115，669，647，616，583，539；HRMS(m/e)理论值：197.0841；实测值：197.2370.；
氮化合物晶体数据如下：
经验式 C13H11NO
分子量 197.23
温度 100(2)K
波长
晶系，空间群 单斜晶系,C2/c
晶胞参数
α＝90°.
体积
电荷密度 4,1.349Mg/m^3
吸收校正参数 0.433 mm^-1
单胞内的电子数目252
晶体大小 0.13x0.06x0.02mm
Theta角的范围 6.591 to 87.656
HKL的指标收集范围 -24<＝h<＝24,-5<k<＝5，-8<l<＝8
收集/独立衍射数据 9677/2563[R(int)＝0.0392]
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557/0/79
精修使用的方法 1.124
衍射点的一致性因子 R1＝0.0520，ωR2＝0.1365
可观察衍射的吻合因子 R1＝0.0549,ωR2＝0.1383
差值傅里叶图上的最大峰顶和峰谷
晶体典型的键长数据：
晶体典型的键角数据：
二苯甲酮亚胺的腈硅化反应应用；
称取0.1mmol配合物，置于25mL小烧瓶中，加入2mL无水甲醇，再向溶液中加入1.0mmol二苯甲酮亚胺和0.3mL三甲基硅腈，常温下搅拌13h，进行1HNMR检测。催化转化率:>99％；1H NMR(600MHz,CDCl3,27℃)δ7.23–7.59(m,10H),4.10(s,2H)。
Claims (4)
1.一种氮苯基苯甲酰胺化合物，其化学式如下：
2.权利要求1所述的晶体化合物(I)，在293(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MoKα射线
以ω-θ扫描方式收集衍射数据，其特征在于晶体属斜方晶系,单斜晶系,C2/c，其晶胞参数：
α＝90°；
β＝107.635(8)°；
γ＝90°。
3.权利要求1所述的晶体化合物(I)的合成方法包括反应、分离和纯化，其特征是无水无氧条件下，称取二苯甲酮肟0.0235g及0.0197g三甲基硅腈和钯配合物0.1147g，放入5.0mL烧瓶中，加入2.0mL二氯甲烷做溶剂，室温搅拌48小时后，柱层析分离，用石油醚/二氯甲烷(3/7)洗脱，将收集的第一组分点自然挥发，柱层析后得氮苯基苯甲酰胺晶体。
4.由权利要求1所述的晶体化合物(I)的用途，是作为催化剂在二苯甲酮亚胺的腈硅化反应中显示了较好的催化性能，其转化率高达99％。
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| CN112174893A (zh) * | 2020-10-15 | 2021-01-05 | 合肥工业大学 | 一种2,4,5-三甲基-1h-咪唑啉甲酸盐的合成方法及用途 |
| CN112430241A (zh) * | 2020-11-20 | 2021-03-02 | 合肥工业大学 | 一种六水合方酸钠配合物 |
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