CN112812032A - Preparation method of acetamide compound - Google Patents
Preparation method of acetamide compound Download PDFInfo
- Publication number
- CN112812032A CN112812032A CN202110068787.5A CN202110068787A CN112812032A CN 112812032 A CN112812032 A CN 112812032A CN 202110068787 A CN202110068787 A CN 202110068787A CN 112812032 A CN112812032 A CN 112812032A
- Authority
- CN
- China
- Prior art keywords
- acetamide compound
- compound
- dimethyl carbonate
- acetamide
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- -1 acetamide compound Chemical class 0.000 title claims abstract description 37
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title abstract description 9
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 claims abstract description 26
- 238000006243 chemical reaction Methods 0.000 claims abstract description 22
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims abstract description 21
- LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 claims abstract description 14
- 150000002828 nitro derivatives Chemical class 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 10
- 235000009518 sodium iodide Nutrition 0.000 claims abstract description 7
- FQNHWXHRAUXLFU-UHFFFAOYSA-N carbon monoxide;tungsten Chemical group [W].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-].[O+]#[C-] FQNHWXHRAUXLFU-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000001488 sodium phosphate Substances 0.000 claims abstract description 6
- 229910000162 sodium phosphate Inorganic materials 0.000 claims abstract description 6
- 239000002904 solvent Substances 0.000 claims abstract description 6
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910001868 water Inorganic materials 0.000 claims abstract description 6
- 229910052703 rhodium Inorganic materials 0.000 claims description 11
- 239000010948 rhodium Substances 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 10
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims description 4
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 4
- 125000001072 heteroaryl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000001424 substituent group Chemical group 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 239000002585 base Substances 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000003446 ligand Substances 0.000 claims 3
- 239000003513 alkali Substances 0.000 claims 2
- 150000003869 acetamides Chemical class 0.000 abstract description 3
- 125000000524 functional group Chemical group 0.000 abstract description 3
- 239000000758 substrate Substances 0.000 abstract description 2
- 239000007805 chemical reaction reactant Substances 0.000 abstract 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 20
- 238000005160 1H NMR spectroscopy Methods 0.000 description 10
- 238000005481 NMR spectroscopy Methods 0.000 description 9
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- 239000002994 raw material Substances 0.000 description 5
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000005910 aminocarbonylation reaction Methods 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000001569 carbon dioxide Substances 0.000 description 2
- 229910002092 carbon dioxide Inorganic materials 0.000 description 2
- 238000005810 carbonylation reaction Methods 0.000 description 2
- 125000004989 dicarbonyl group Chemical group 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 1
- 229910021604 Rhodium(III) chloride Inorganic materials 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 125000005002 aryl methyl group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000006315 carbonylation Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000012790 confirmation Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229910017053 inorganic salt Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910001496 lithium tetrafluoroborate Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000006063 methoxycarbonylation reaction Methods 0.000 description 1
- 230000001035 methylating effect Effects 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012038 nucleophile Substances 0.000 description 1
- 238000012805 post-processing Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
- C07D317/66—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention discloses a preparation method of an acetamide compound, which comprises the following steps: the method comprises the following steps of reacting tetracarbonyl dirhodium dichloride, 1, 3-bis (diphenylphosphino) propane, tungsten carbonyl, sodium phosphate, sodium iodide, water, a nitro compound and dimethyl carbonate at 120 ℃ for 24 hours, and carrying out post-treatment after the reaction is completed to obtain the acetamide compound. The preparation method uses dimethyl carbonate as a C1 source and a green solvent, has simple operation, cheap and easily obtained reaction starting materials, wide tolerance range of substrate functional groups and high reaction efficiency. Can synthesize a plurality of acetamide compounds according to actual needs, is convenient to operate and widens the practicability of the method.
Description
Technical Field
The invention belongs to the field of organic synthesis, and particularly relates to a preparation method of an acetamide compound.
Background
Dimethyl carbonate is a low-toxicity and biodegradable compound, can be obtained by converting carbon dioxide in the atmosphere, is often used as a green solvent in organic synthesis (chem. Rev.2010,110,4554-4581), and has a very wide development prospect. Meanwhile, dimethyl carbonate is used as an important organic synthesis intermediate and has wide application in industry and fine chemistry. Under different reaction conditions, dimethyl carbonate can be used as a methoxycarbonylation reagent and also can be used as a methylation reagent to react with various nucleophiles (Green chem.2018,20, 28-85). Conventional methylating agents such as diazomethane, dimethyl sulfate, methyl iodide and the like mostly have the defects of explosiveness, toxicity/corrosiveness, high price and the like. In addition, in these methylation reactions, a stoichiometric amount of base is usually required, resulting in the generation of useless inorganic salts that require disposal. Because the dimethyl carbonate is non-toxic and environment-friendly, the dimethyl carbonate can be used as a safe and environment-friendly methyl substitute, no unnecessary inorganic salt is generated in the reaction, and the methanol and the carbon dioxide released after the reaction can be recycled and reused for synthesizing the dimethyl carbonate. Therefore, the excellent environmental protection characteristic and the diversified reactivity of the dimethyl carbonate make the dimethyl carbonate as an ideal synthetic reagent and also have a development prospect as a reaction medium, and further development is needed.
In addition, transition metal catalyzed carbonylation reactions have dramatically progressed over the past few decades and have been widely used in the production of carbonyl-containing compounds. The most representative example is the synthesis of acetic acid (Monsanto process). HI is often used as a cocatalyst during the reaction, with severe corrosive effects on the equipment. Recently, Han and coworkers developed LiI and LiBF4Promoted RhCl3A novel route to aryl acetates by catalyzed carbonylation of aryl methyl ethers. Therefore, the development of new methods for constructing carbonyl-containing compounds is urgent and attracts a great deal of attention from a great number of organic synthetic chemists.
Based on this, we developed a rhodium-catalyzed aminocarbonylation reaction to an acetamide compound. To our knowledge, this is the first aminocarbonylation reaction using dimethyl carbonate as both a source of C1 and a green solvent, with a cheap and readily available nitro compound as a nitrogen substitute. Dimethyl carbonate is used in rhodium-catalyzed amino carbonylation reaction, a new and sustainable approach is developed for the construction of acetamide compounds, and positive influence is generated on the future synthesis of carbonyl-containing compounds.
Disclosure of Invention
The invention provides a preparation method of an acetamide compound, which has simple steps, cheap and easily-obtained reaction raw materials, compatibility with various functional groups and good reaction applicability, and provides a new direction for the synthesis of an acetamide compound by taking dimethyl carbonate as a C1 source and a green solvent.
A method for preparing an acetamide compound, comprising the steps of: reacting a rhodium catalyst, 1, 3-bis (diphenylphosphino) propane, tungsten carbonyl, sodium phosphate, sodium iodide, water, a nitro compound and dimethyl carbonate at 110-130 ℃ for 20-28 hours, and performing post-treatment after complete reaction to obtain the acetamide compound;
the structure of the nitro compound is shown as the formula (II):
RNO2 (II)；
the structure of the dimethyl carbonate is shown as a formula (III):
the structure of the acetamide compound is shown as the formula (I):
in the formulae (I) to (III), R is C3-C6Alkyl, substituted or unsubstituted aryl, heteroaryl, naphthyl;
the substituent on the aryl is C1～C2Alkoxy, trifluoromethyl, halogen, methyl, thiomethyl, or acetyl.
The molar ratio of the rhodium catalyst, the 1, 3-bis (diphenylphosphino) propane, the sodium phosphate, the sodium iodide and the water is 0.02:0.06:1.5:0.3: 2;
the substitution position on the aryl group of R may be ortho, para or meta.
The reaction formula is as follows:
in the present invention, the optional post-processing procedure includes: filtering, mixing the sample with silica gel, and finally purifying by column chromatography to obtain the corresponding acetamide compound, wherein the column chromatography purification is a technical means commonly used in the field.
Preferably, R is tert-butyl, cyclohexyl, substituted or unsubstituted phenyl, heteroaryl, naphthyl; the substituent on the aryl is methoxy, ethoxy, trifluoromethyl, F, Cl, Br, methyl, thiomethyl or acetyl, in this case, the nitro compound is easily obtained, and the reaction yield is high.
The nitro compound and dimethyl carbonate used for the preparation of the acetamide compound are relatively inexpensive and widely occur in nature, and preferably, the nitro compound: the catalyst is 1: 0.01-0.05; as a further preference, the nitro compound: catalyst 1: 0.02.
Preferably, the reaction time is 24 hours, and if the reaction time is too long, the reaction cost is increased, and conversely, it is difficult to ensure the completion of the reaction.
The dosage of the dimethyl carbonate can be used for better dissolving the raw materials, and the dosage of the dimethyl carbonate used by 0.5mmol of nitro compound is about 1-3 mL.
Preferably, the rhodium catalyst is rhodium dicarbonyl dichloride, among the rhodium catalysts, rhodium tetracarbonyl dichloride is relatively cheap, and the reaction efficiency is high when rhodium tetracarbonyl dichloride is used as the catalyst.
Further preferably, the acetamide compound is one of compounds represented by the formulae (I-1) to (I-5):
the compounds represented by the formulae (I-1) to (I-5) are known compounds.
In the above preparation method, the nitro compound, dimethyl carbonate, tungsten carbonyl, dicarbonyl dihidromethyl, 1, 3-bis (diphenylphosphino) propane, sodium phosphate and sodium iodide are generally commercially available products and can be conveniently obtained from the market.
Compared with the prior art, the invention has the beneficial effects that: dimethyl carbonate is used as a C1 source and a green solvent, the preparation method is simple, the operation is easy, the post-treatment is simple and convenient, the reaction starting raw materials are cheap and easy to obtain, the tolerance range of substrate functional groups is wide, and the reaction efficiency is high. Can synthesize various acetamide compounds according to actual needs, and has strong practicability.
Detailed Description
The invention is further described with reference to specific examples.
Examples 1 to 15
Adding dicarbonyl dihidromethodium chloride, 1, 3-bis (diphenylphosphino) propane (DPPP), tungsten carbonyl, sodium phosphate, sodium iodide, water, nitro compound (II) and dimethyl carbonate (III) into a 15mL sealed tube according to the raw material ratio shown in Table 1, uniformly mixing and stirring, reacting according to the reaction conditions shown in Table 2, filtering after the reaction is finished, mixing silica gel, and purifying by column chromatography to obtain a corresponding acetamide compound (I), wherein the reaction process is shown as the following formula:
TABLE 1 raw material addition amounts of examples 1 to 15
TABLE 2
In tables 1 and 2, T is the reaction temperature, T is the reaction time, Et is ethyl, Ph is phenyl, CF3Is trifluoromethyl, Me is methyl, SMe is methylthio, OMe is methoxy and t-Bu is tert-butyl.
Structure confirmation data of the compounds prepared in examples 1 to 5:
nuclear magnetic resonance of the acetamide Compound (I-1) prepared in example 1: (1H NMR and13c NMR) the data were:
1H NMR(400MHz,CDCl3)δ7.96(s,1H),7.36(d,J＝8.9Hz,2H),6.79(d,J＝8.9Hz,2H),3.97(q,J＝7.0Hz,2H),2.09(s,3H),1.37(t,J＝7.0Hz,3H).
13C NMR(101MHz,CDCl3)δ168.9,155.5,131.0,122.0,114.5,63.5,23.9,14.7.
nuclear magnetic resonance of acetamide Compound (I-2) obtained in example 2: (1HNMR and13CNMR) detection data were:
1H NMR(400MHz,CDCl3)δ7.71(s,1H),7.63(d,J＝8.4Hz,2H),7.55(d,J＝8.6Hz,2H),2.20(s,3H).
13C NMR(101MHz,CDCl3)δ168.8,140.9,126.2(d,J＝3.4Hz),125.9,124.1(q,J＝271.5Hz),119.4,24.6.
nuclear magnetic resonance of acetamide Compound (I-3) obtained in example 3: (1H NMR and13c NMR) the data were:
1H NMR(400MHz,CDCl3)δ7.45(d,J＝8.7Hz,2H),7.34(s,1H),7.27(d,J＝7.8Hz,2H),2.17(s,3H).
13C NMR(101MHz,CDCl3)δ168.3,136.4,129.3,129.0,121.1,24.6.
nuclear magnetic resonance of acetamide Compound (I-4) obtained in example 4: (1H NMR and13c NMR) the data were:
1H NMR(400MHz,CDCl3)δ8.07(s,1H),7.15(s,1H),6.77(d,J＝7.5Hz,1H),6.68(d,J＝7.9 Hz,1H),5.90(s,2H),2.09(s,3H).
13C NMR(101MHz,CDCl3)δ168.6,147.6,144.2,132.1,113.4,107.9,103.1,101.2,24.2.
nuclear magnetic resonance of acetamide Compound (I-5) obtained in example 5: (1H NMR and13c NMR) the data were:
1H NMR(400MHz,CDCl3)δ5.49(s,1H),3.78–3.66(m,1H),1.93(s,3H),1.89(dd,J＝12.5,3.3Hz,2H),1.73–1.65(m,2H),1.63–1.56(m,1H),1.40–1.27(m,2H),1.20–1.03(m,3H).
13C NMR(101MHz,CDCl3)δ169.2,48.2,33.1,25.5,24.9,23.5.
Claims (8)
1. a method for preparing an acetamide compound, comprising the steps of: reacting a rhodium catalyst, a ligand, tungsten carbonyl, alkali, sodium iodide, water, a nitro compound and dimethyl carbonate at 110-130 ℃ for 20-28 hours, and after the reaction is completed, performing post-treatment to obtain the acetamide compound;
the structure of the nitro compound is shown as the formula (II):
RNO2 (II)；
the structure of the dimethyl carbonate is shown as a formula (III):
the structure of the acetamide compound is shown as the formula (I):
in the formulas (I) to (III), R is C3-C6Alkyl, substituted or unsubstituted aryl, heteroaryl;
the substituent on the aryl is C1～C2Alkoxy, trifluoromethyl, halogen, methyl, thiomethyl, or acetyl.
2. The method for producing an acetamide compound of claim 1 wherein R is t-butyl, cyclohexyl, substituted or unsubstituted phenyl, heteroaryl, naphthyl;
and the substituent on the phenyl is methoxy, ethoxy, trifluoromethyl, F, Cl, Br, methyl, thiomethyl or acetyl.
3. The method for producing an acetamide compound according to claim 1 wherein, on a molar basis, the nitro compound: tungsten carbonyl: rhodium catalyst: ligand: alkali: sodium iodide: water is 1: 1.5-2: 0.01-0.05: 0.03-0.2: 1-2: 0-0.5: 1-2.
4. The method for producing an acetamide compound of claim 1 wherein the reaction uses dimethyl carbonate as a solvent.
5. The method of claim 1, wherein the rhodium catalyst is rhodium tetracarbonyl dichloride.
6. The method for producing an acetamide compound of claim 1 where the ligand is 1, 3-bis (diphenylphosphino) propane.
7. The method of claim 1, wherein the base is sodium phosphate.
8. The method for preparing an acetamide compound of claim 1, wherein the acetamide compound is one of the compounds of formula (I-1) to formula (I-5):
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110068787.5A CN112812032B (en) | 2021-01-19 | 2021-01-19 | Preparation method of acetamide compound |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202110068787.5A CN112812032B (en) | 2021-01-19 | 2021-01-19 | Preparation method of acetamide compound |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN112812032A true CN112812032A (en) | 2021-05-18 |
| CN112812032B CN112812032B (en) | 2022-07-19 |
Family
ID=75870102
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202110068787.5A Active CN112812032B (en) | 2021-01-19 | 2021-01-19 | Preparation method of acetamide compound |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN112812032B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113896648A (en) * | 2021-09-29 | 2022-01-07 | 浙江理工大学 | Preparation method of alpha, beta-unsaturated amide compound |
| CN115246757A (en) * | 2022-01-07 | 2022-10-28 | 浙江理工大学 | Preparation method of aryl acetamide compound |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111978194A (en) * | 2020-08-14 | 2020-11-24 | 浙江理工大学 | Preparation method of aryl acetamide compound |
-
2021
- 2021-01-19 CN CN202110068787.5A patent/CN112812032B/en active Active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111978194A (en) * | 2020-08-14 | 2020-11-24 | 浙江理工大学 | Preparation method of aryl acetamide compound |
Non-Patent Citations (1)
| Title |
|---|
| ZHI-PENG BAO ET AL.: "A novel construction of acetamides from rhodium-catalyzed aminocarbonylation of DMC with nitro compounds", 《CHEMCOMM》 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN113896648A (en) * | 2021-09-29 | 2022-01-07 | 浙江理工大学 | Preparation method of alpha, beta-unsaturated amide compound |
| CN113896648B (en) * | 2021-09-29 | 2023-08-18 | 浙江理工大学 | Preparation method of alpha, beta-unsaturated amide compound |
| CN115246757A (en) * | 2022-01-07 | 2022-10-28 | 浙江理工大学 | Preparation method of aryl acetamide compound |
| CN115246757B (en) * | 2022-01-07 | 2023-10-20 | 浙江理工大学 | Preparation method of aryl acetamide compound |
Also Published As
| Publication number | Publication date |
|---|---|
| CN112812032B (en) | 2022-07-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN112812032B (en) | Preparation method of acetamide compound | |
| CN112898192B (en) | Preparation method of N-acyl indole compound | |
| CN113045489B (en) | Preparation method of 3-arylquinoline-2 (1H) ketone derivative | |
| CN114539198B (en) | Preparation method of amide compound containing (iso) chroman structure | |
| CN114478375B (en) | Preparation method of 3-alkenyl quinoline-2 (1H) ketone derivative | |
| CN114195711B (en) | Preparation method of quinoline-4 (1H) -ketone compound | |
| CN115260080B (en) | Preparation method of indole-3-formamide compound | |
| CN111423351B (en) | Chiral copper compound and preparation method and application thereof | |
| CN113511986B (en) | Preparation method of aryl acetonitrile derivative | |
| CN111978194B (en) | Preparation method of aryl acetamide compound | |
| CN112694430B (en) | Preparation method of 1, 5-dihydro-2H-pyrrole-2-ketone compound | |
| CN115772157A (en) | Preparation method of 2-alkoxy indole compound | |
| CN108727179B (en) | Synthetic method of alpha-allyl substituted alpha, beta-unsaturated ketone, ester or nitrile compound | |
| CN113896648B (en) | Preparation method of alpha, beta-unsaturated amide compound | |
| CN115246757B (en) | Preparation method of aryl acetamide compound | |
| CN110078608B (en) | Method for synthesizing 2-benzyl-2-ethyl pentanal through beta-position derivatization reaction of aliphatic aldehyde | |
| CN113735826B (en) | Preparation method of 3-benzylidene-2, 3-dihydroquinolone compound | |
| CN115286553B (en) | Preparation method of indole compound | |
| CN115286628B (en) | Preparation method of indolo [2,1a ] isoquinoline compound | |
| CN115197124B (en) | Method for synthesizing polysubstituted pyridine derivative based on alpha, beta-unsaturated oxime ester under catalysis of ammonium iodide | |
| CN114751883B (en) | Preparation method of benzofuran-3-carboxamide compound | |
| CN115246807B (en) | Preparation method of thioester compound containing (iso) chroman structure | |
| CN115286556B (en) | Preparation method of ester compound containing indolone or isoquinoline-1, 3-dione structure | |
| CN114773242B (en) | Preparation method of alpha, beta-unsaturated thioester compound | |
| CN117164544A (en) | Preparation method of pyrone derivative containing carboxamide structure |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20240521 Address after: Room 802, Building C, Qingwang Science and Technology Park, Baohe Economic Development Zone, Hefei City, Anhui Province, 230041 Patentee after: Hefei xingzhicheng Information Technology Co.,Ltd. Country or region after: China Address before: 310018 No. 2 street, Baiyang street, Hangzhou economic and Technological Development Zone, Zhejiang 928 Patentee before: ZHEJIANG SCI-TECH University Country or region before: China |
|
| TR01 | Transfer of patent right |
Effective date of registration: 20240603 Address after: No. 237-4-2 Pengliuyang Road, Wuchang District, Wuhan City, Hubei Province, 430060 Patentee after: An Feng Country or region after: China Address before: Room 802, Building C, Qingwang Science and Technology Park, Baohe Economic Development Zone, Hefei City, Anhui Province, 230041 Patentee before: Hefei xingzhicheng Information Technology Co.,Ltd. Country or region before: China |