JPH0374210B2 - - Google Patents
Info
- Publication number
- JPH0374210B2 JPH0374210B2 JP59021378A JP2137884A JPH0374210B2 JP H0374210 B2 JPH0374210 B2 JP H0374210B2 JP 59021378 A JP59021378 A JP 59021378A JP 2137884 A JP2137884 A JP 2137884A JP H0374210 B2 JPH0374210 B2 JP H0374210B2
- Authority
- JP
- Japan
- Prior art keywords
- general formula
- monoalkylamides
- represented
- group
- present
- 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.)
- Expired - Lifetime
Links
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 10
- 150000001408 amides Chemical class 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- -1 n-octyl Chemical group 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000000034 method Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- LSBDFXRDZJMBSC-UHFFFAOYSA-N 2-phenylacetamide Chemical compound NC(=O)CC1=CC=CC=C1 LSBDFXRDZJMBSC-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QDHFDXDMKYJPSC-UHFFFAOYSA-N N-ethylphenylacetamide Chemical compound CCNC(=O)CC1=CC=CC=C1 QDHFDXDMKYJPSC-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- QJGWNDLRYDTKEI-UHFFFAOYSA-N n-butylbutanamide Chemical compound CCCCNC(=O)CCC QJGWNDLRYDTKEI-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
- 125000006040 2-hexenyl group Chemical group 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001326 naphthylalkyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 125000004344 phenylpropyl group Chemical group 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Description
技術分野
本発明は、Ｎ−モノアルキルアミド類の製造法
に関する。更に詳しくは、本発明は、一般式
R1CONHR2 （）
［式中R1はアルキル基、アリール基又はアラル
キル基を示す。R2はアルキル基、アルケニル基
又はアラルキル基を示す。］で表わされるＮ−モ
ノアルキルアミド類の製造法に関する。
発明の目的及び構成
本発明の目的は、上記一般式（）で表わされ
るＮ−モノアルキルアミド類を選択的に合成し
得、従つて該アミド類を高収率、高純度で製造し
得る方法を提供することにある。
本発明の方法によれば、上記一般式（）のＮ
−モノアルキルアミド類は、アルミナ及びアルカ
リの共存下に一般式
R1CONH2 （）
［式中R1は前記に同じ。］で表わされるアミド類
と一般式
R2X （）
［式中Ｘはハロゲン原子を示す。R2は前記に同
じ。］で表わされるハロゲン化物とを反応させる
ことにより製造される。
本発明において出発原料として用いられる一般
式（）のアミド類及び一般式（）のハロゲン
化物は、いずれも公知の化合物である。本明細書
においてR1及びR2で示されるアルキル基として
は、例えばメチル、エチル、ｎ−プロピル、イソ
プロピル、ｎ−ブチル、イソブチル、tert−ブチ
ル、ｎ−ペンチル、ｎ−ヘキシル、ｎ−ヘプチ
ル、ｎ−オクチル、ｎ−デシル、ｎ−ドデシル、
ｎ−ヘキサデシル、ｎ−オクタデシル基等が挙げ
られる。R1で示されるアリール基としては、例
えば置換基を有し又は有さないフエニル基、置換
基を有し又は有さないナフチル基等が挙げられ
る。R1及びR2で示されるアラルキル基としては、
芳香環上に置換基を有し又は有さないベンジル
基、フエネチル基、フエニルプロピル基等のフエ
ニルアルキル基、芳香環上に置換基を有し又は有
さないナフチルアルキル基等が挙げられる。R2
で示されるアルケニル基としては、例えばビニ
ル、アリル、２−ブテニル、３−ブテニル、１−
メチルアリル、２−ヘキセニル基等が挙げられ
る。上記における置換基としては、ハロゲン原
子、ニトロ基、アミノ基、アルキル基、アルコキ
シ基等が例示される。またＸで示されるハロゲン
原子としては、例えば塩素原子、臭素原子、沃素
原子等が挙げられる。
本発明において一般式（）のアミド類と一般
式（）のハロゲン化物との使用割合としては、
特に制限がなく広い範囲内から適宜選択すること
ができるが、通常前者に対して後者を少なくとも
等モル程度、好ましくは1.1〜1.5倍モル程度用い
るのがよい。
本発明では、反応系内にアルミナ及びアルカリ
を存在させる。またアルカリとしては、例えば水
酸化カリウム、水酸化ナトリウム、水酸化リチウ
ム等のアルカリ金属水酸化物、水酸化マグネシウ
ム、水酸化カルシウム等のアルカリ土類金属水酸
化物、炭酸カリウム、炭酸ナトリウム等のアルカ
リ金属炭酸塩、炭酸水素カリウム、炭酸水素ナト
リウム等のアルカリ金属重炭酸塩等を挙げること
ができる。本発明においては、上記アルミナ及び
アルカリは、これらを混合物として使用してもよ
いし、アルミナにアルカリを担持させた形態で使
用してもよい。アルミナ及びアルカリの使用量と
しては、特に制限されることなく広い範囲内から
適宜選択することができる。本発明では、原料で
ある一般式（）のアミド類１モルに対して、ア
ルミナを通常100〜2000ｇ程度、好ましくは500〜
1500ｇ程度用い、またアルカリを通常１〜20モル
程度、好ましくは３〜５モル程度用いるのがよ
い。
本発明の反応は、一般に適当な溶媒中にて行な
われる。溶媒としては、本発明の反応に悪影響を
及ぼさない限り従来公知のものを広く使用でき、
例えばジオキサン、テトラヒドロフラン、エチル
エーテル等のエーテル類、ベンゼン、トルエン、
キシレン等の芳香族炭化水素類、ヘキサン、シク
ロヘキサン等の飽和炭化水素流等が挙げられる。
これらの中でジオキサン、テトラヒドロフラン及
びベンゼンが特に好ましい。上記反応は、室温下
及び加温下のいずれでも進行するが、通常室温〜
100℃程度にて好適に進行し、一般に３〜12時間
程度にて反応は完結する。
上記反応終了後に、固形分を去し、液から
溶媒を留去することにより、純度97％以上の一般
式（）のＮ−モノアルキルアミド類が収得され
る。未反応の一般式（）のアミド類は、アルミ
ナに吸着されているので高回収率で回収でき、再
使用することができる。より一層の純度を所望す
るのであれば、再結晶、カラムクロマトグラフイ
ー等の常法の精製手段を採用すればよい。
実施例
実施例 １
85％水酸化カリウム3.3ｇ（50ミリモル）をア
ルミナ（メルク社、Type60、塩基性、活性度Ｉ、
70〜230メツシユ）10ｇに担持させたもの、２−
フエニルアセトアミド1.35ｇ（10ミリモル）、臭
化エチル1.3ｇ（12ミリモル）及びジオキサン20
mlの混合液を60℃にて８時間激しく撹拌した。こ
の反応液を分析（GLC）したところ、目的とす
るＮ−エチル−２−フエニルアセトアミドの選択
率は97.5％であつた。固形分を去し、ベンゼン
（30ml×２）で洗浄後溶媒を留去して、Ｎ−エチ
ル−２−フエニルアセトアミド1.25ｇ（収率77
％、純度97％）を得た。これをエーテル−ヘキサ
ンより再結晶すると、純度を99％以上にすること
ができた。
実施例 ２
85％水酸化カリウム3.3ｇ（50ミリモル）及び
アルミナ（メルク社、Type90、中性、活性度Ｉ、
70〜230メツシユ）10ｇを乳鉢で粉砕したもの、
ｎ−ブタンアミド0.87ｇ（10ミリモル）、臭化ブ
チル1.7ｇ（12ミリモル）及びジオキサンの混合
液を60℃にて８時間激しく撹拌した。この反応液
を分析（GLC）したところ、Ｎ−ブチルブタン
アミドの選択率は99.6％であつた。固形分を去
し、ベンゼン（30ml×２）で洗浄後溶媒を留去し
て、Ｎ−ブチルブタンアミド1.2ｇ（収率80％、
純度97％）を得た。
下記第１表に示すアミド類（）及びハロゲン
化物（）を用い、上記実施例２と同様にして目
的とするＮ−モノアルキルアミド類（）を得
た。第１表に反応温度、目的物の選択率（％）
（反応液のGLC分析による）及び目的物の収率
（％）を示す。尚第１表で得られる目的化合物の
純度は、いずれも純度97％以上であつた。第１表
中Phはフエニル基を意味する。
TECHNICAL FIELD The present invention relates to a method for producing N-monoalkylamides. More specifically, the present invention provides a compound having the general formula R 1 CONHR 2 () [wherein R 1 represents an alkyl group, an aryl group, or an aralkyl group]. R 2 represents an alkyl group, an alkenyl group or an aralkyl group. ] The present invention relates to a method for producing N-monoalkylamides represented by the following. Object and Structure of the Invention An object of the present invention is a method capable of selectively synthesizing N-monoalkylamides represented by the above general formula () and thus producing the amides in high yield and high purity. Our goal is to provide the following. According to the method of the present invention, N of the above general formula ()
- Monoalkylamides are prepared by the general formula R 1 CONH 2 () in the coexistence of alumina and an alkali, where R 1 is the same as above. ] Amides represented by the general formula R 2 X ( ) [wherein X represents a halogen atom. R 2 is the same as above. ] It is produced by reacting with a halide represented by: Amides of general formula () and halides of general formula () used as starting materials in the present invention are both known compounds. In this specification, examples of the alkyl group represented by R 1 and R 2 include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-decyl, n-dodecyl,
Examples include n-hexadecyl and n-octadecyl groups. Examples of the aryl group represented by R 1 include a phenyl group with or without a substituent, a naphthyl group with or without a substituent, and the like. As the aralkyl group represented by R 1 and R 2 ,
Examples include phenylalkyl groups such as benzyl, phenethyl, and phenylpropyl groups with or without a substituent on the aromatic ring, and naphthylalkyl groups with or without a substituent on the aromatic ring. . R2
Examples of the alkenyl group represented by include vinyl, allyl, 2-butenyl, 3-butenyl, 1-
Examples include methylallyl and 2-hexenyl group. Examples of the above substituents include halogen atoms, nitro groups, amino groups, alkyl groups, and alkoxy groups. Examples of the halogen atom represented by X include chlorine atom, bromine atom, and iodine atom. In the present invention, the ratio of the amides of general formula () to the halides of general formula () is as follows:
Although there are no particular limitations and they can be appropriately selected from within a wide range, it is generally advisable to use at least an equimolar amount of the latter to the former, preferably about 1.1 to 1.5 times the molar amount. In the present invention, alumina and alkali are present in the reaction system. Examples of alkalis include alkali metal hydroxides such as potassium hydroxide, sodium hydroxide, and lithium hydroxide; alkaline earth metal hydroxides such as magnesium hydroxide and calcium hydroxide; and alkalis such as potassium carbonate and sodium carbonate. Examples include metal carbonates, alkali metal bicarbonates such as potassium hydrogen carbonate, and sodium hydrogen carbonate. In the present invention, the above-mentioned alumina and alkali may be used as a mixture or in the form of alumina supporting an alkali. The amounts of alumina and alkali to be used are not particularly limited and can be appropriately selected from a wide range. In the present invention, alumina is usually added in an amount of about 100 to 2000 g, preferably 500 to 2000 g, per mole of the amide of the general formula () as a raw material.
It is preferable to use about 1,500 g of alkali, and usually about 1 to 20 moles, preferably about 3 to 5 moles of alkali. The reactions of the invention are generally carried out in a suitable solvent. As the solvent, a wide variety of conventionally known solvents can be used as long as they do not adversely affect the reaction of the present invention.
For example, dioxane, tetrahydrofuran, ethers such as ethyl ether, benzene, toluene,
Examples include aromatic hydrocarbons such as xylene, saturated hydrocarbon streams such as hexane, cyclohexane, and the like.
Among these, dioxane, tetrahydrofuran and benzene are particularly preferred. The above reaction proceeds both at room temperature and under heating, but usually from room temperature to
The reaction proceeds suitably at about 100°C and is generally completed in about 3 to 12 hours. After the completion of the above reaction, the solid content is removed and the solvent is distilled off from the liquid to obtain the N-monoalkylamides of the general formula () with a purity of 97% or more. Since the unreacted amides of general formula () are adsorbed on alumina, they can be recovered with a high recovery rate and reused. If higher purity is desired, conventional purification methods such as recrystallization and column chromatography may be used. Examples Example 1 3.3 g (50 mmol) of 85% potassium hydroxide was added to alumina (Merck & Co., Type 60, basic, activity I,
70-230 mesh) supported on 10g, 2-
Phenylacetamide 1.35 g (10 mmol), ethyl bromide 1.3 g (12 mmol) and dioxane 20
ml of the mixture was vigorously stirred at 60°C for 8 hours. When this reaction solution was analyzed (GLC), the selectivity of the target N-ethyl-2-phenylacetamide was 97.5%. After removing the solid content and washing with benzene (30 ml x 2), the solvent was distilled off to give 1.25 g of N-ethyl-2-phenylacetamide (yield 77
%, purity 97%). When this was recrystallized from ether-hexane, the purity could be increased to over 99%. Example 2 3.3 g (50 mmol) of 85% potassium hydroxide and alumina (Merck & Co., Type 90, neutral, activity I,
70-230 mesh) 10g crushed in a mortar,
A mixture of 0.87 g (10 mmol) of n-butanamide, 1.7 g (12 mmol) of butyl bromide, and dioxane was vigorously stirred at 60° C. for 8 hours. When this reaction solution was analyzed (GLC), the selectivity for N-butylbutanamide was 99.6%. After removing the solid content and washing with benzene (30 ml x 2), the solvent was distilled off to obtain 1.2 g of N-butylbutanamide (yield: 80%,
purity of 97%) was obtained. Using the amides () and halides () shown in Table 1 below, the desired N-monoalkylamides () were obtained in the same manner as in Example 2 above. Table 1 shows the reaction temperature and target product selectivity (%).
(Based on GLC analysis of the reaction solution) and the yield (%) of the target product are shown. The purity of the target compounds obtained in Table 1 was all 97% or higher. In Table 1, Ph means a phenyl group.
【表】
発明の効果
本発明の方法によれば、目的とする一般式
（）のＮ−モノアルキルアミド類を選択的に合
成し得、それ故該アミド類を簡便な操作により高
収率、高純度で製造し得る。従つて本発明の方法
は、一般式（）のＮ−モノアルキルアミド類の
工業的製造法として極めて有効である。[Table] Effects of the Invention According to the method of the present invention, the desired N-monoalkylamides of the general formula () can be selectively synthesized, and therefore, the amides can be synthesized in high yields and with simple operations. Can be produced with high purity. Therefore, the method of the present invention is extremely effective as an industrial method for producing N-monoalkylamides of general formula ().
Claims (1)
キル基を示す。」 で表わされるアミド類と一般式 R2X ［式中R2はアルキル基、アルケニル基又はアラ
ルキル基を示す。Ｘはハロゲン原子を示す。］ で表わされるハロゲン化物とを反応させて一般式 R1CONHR2 ［式中R1及びR2は前記に同じ。］ で表わされるＮ−モノアルキルアミド類を得るこ
とを特徴とするＮ−モノアルキルアミド類の製造
法。[Claims] 1. In the coexistence of alumina and an alkali, a compound of the general formula R 1 CONH 2 [wherein R 1 represents an alkyl group, an aryl group, or an aralkyl group]. Amides represented by the general formula R 2 X [wherein R 2 represents an alkyl group, an alkenyl group or an aralkyl group]. X represents a halogen atom. ] by reacting with a halide represented by the general formula R 1 CONHR 2 [wherein R 1 and R 2 are the same as above. ] A method for producing N-monoalkylamides, which comprises obtaining N-monoalkylamides represented by the following.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2137884A JPS60166649A (en) | 1984-02-07 | 1984-02-07 | Preparation of n-monoalkylamide |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2137884A JPS60166649A (en) | 1984-02-07 | 1984-02-07 | Preparation of n-monoalkylamide |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS60166649A JPS60166649A (en) | 1985-08-29 |
| JPH0374210B2 true JPH0374210B2 (en) | 1991-11-26 |
Family
ID=12053426
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2137884A Granted JPS60166649A (en) | 1984-02-07 | 1984-02-07 | Preparation of n-monoalkylamide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS60166649A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2013180983A (en) * | 2012-03-01 | 2013-09-12 | Tokyo Univ Of Agriculture & Technology | Method of manufacturing n-substituted amide compound |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5920259A (en) * | 1982-07-22 | 1984-02-01 | Mitsui Toatsu Chem Inc | Preparation of n-substituted amide compound |
| JPS5920258A (en) * | 1982-07-22 | 1984-02-01 | Mitsui Toatsu Chem Inc | Preparation of n-substituted alkoxycarboxylic acid amide compound |
-
1984
- 1984-02-07 JP JP2137884A patent/JPS60166649A/en active Granted
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5920259A (en) * | 1982-07-22 | 1984-02-01 | Mitsui Toatsu Chem Inc | Preparation of n-substituted amide compound |
| JPS5920258A (en) * | 1982-07-22 | 1984-02-01 | Mitsui Toatsu Chem Inc | Preparation of n-substituted alkoxycarboxylic acid amide compound |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS60166649A (en) | 1985-08-29 |
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