KR810001319B1 - Process for the preparation of new isobutyramide derivatives - Google Patents
Process for the preparation of new isobutyramide derivatives Download PDFInfo
- Publication number
- KR810001319B1 KR810001319B1 KR7700639A KR770000639A KR810001319B1 KR 810001319 B1 KR810001319 B1 KR 810001319B1 KR 7700639 A KR7700639 A KR 7700639A KR 770000639 A KR770000639 A KR 770000639A KR 810001319 B1 KR810001319 B1 KR 810001319B1
- Authority
- KR
- South Korea
- Prior art keywords
- isobutyramid
- bromo
- formula
- isobutyramide
- derivatives
- 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
Links
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical class CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 title claims description 3
- 238000000034 method Methods 0.000 title description 3
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000012454 non-polar solvent Substances 0.000 claims description 2
- NESLWCLHZZISNB-UHFFFAOYSA-M sodium phenolate Chemical class [Na+].[O-]C1=CC=CC=C1 NESLWCLHZZISNB-UHFFFAOYSA-M 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Natural products CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- WXNZTHHGJRFXKQ-UHFFFAOYSA-N 4-chlorophenol Chemical compound OC1=CC=C(Cl)C=C1 WXNZTHHGJRFXKQ-UHFFFAOYSA-N 0.000 description 2
- 238000010533 azeotropic distillation Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- FOCDNGFPPIOJTN-UHFFFAOYSA-N 1-bromo-1-chloro-2-methylpropane Chemical compound CC(C)C(Cl)Br FOCDNGFPPIOJTN-UHFFFAOYSA-N 0.000 description 1
- MEFHXBQPHHVGHF-UHFFFAOYSA-N 2-bromo-n-(4-cyanobutyl)-2-methylpropanamide Chemical compound CC(C)(Br)C(=O)NCCCCC#N MEFHXBQPHHVGHF-UHFFFAOYSA-N 0.000 description 1
- RHMPLDJJXGPMEX-UHFFFAOYSA-N 4-fluorophenol Chemical compound OC1=CC=C(F)C=C1 RHMPLDJJXGPMEX-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- -1 N-cyanoethyl-α-bromo-isobutyramid Chemical compound 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
내용 없음.No content.
Description
본 발명은 일반식(가)의 신규한 이소부티라미드류 및 그 산부가염의 제조에 관한 것이다.The present invention relates to the production of novel isobutyramides of the general formula (A) and acid addition salts thereof.
식중, R1은 할로겐 원자이고, n은 2-6인 정수이다.Wherein R 1 is a halogen atom and n is an integer of 2-6.
본 발명의 신규한 화합물은 일반식(1)에 상응하는 치환 소디움페놀레이트와 일반식(2)의 적당한 N-시아노알킬 α-브로모-이소부티라미드를 비극성용매에서 반응시켜서 제조한다.The novel compounds of the present invention are prepared by reacting a substituted sodium phenolate corresponding to formula (1) with a suitable N-cyanoalkyl α-bromo-isobutyramid of formula (2) in a nonpolar solvent.
식중, R1과 n은 상기 정의와 같다.Wherein R 1 and n are as defined above.
일반식(2)의 N-시아노알킬 α-브로모-이소부티라미드는 하기 반응식에 따라, α-브로모-이소부틸클로라이드와 적당한 아미노알킬니트릴의 반응에 의해서 쉽게 제조할 수 있다.N-cyanoalkyl α-bromo-isobutyramid of formula (2) can be easily prepared by reaction of α-bromo-isobutylchloride with an appropriate aminoalkylnitrile according to the following scheme.
그 합성은 소디움펜에이트로 전환된 적당한 치환페놀과 나트륨을 에탄올을 함유한 용액에서 반응시킴이 바람직하다. 에탄올을 톨루엔으로 대치시키고, 과량의 톨루엔을 첨가한 후, 이어서 공비(共沸)증류한다.The synthesis is preferably reacted with a suitable substituted phenol converted to sodium penate and sodium in a solution containing ethanol. Ethanol is replaced with toluene, excess toluene is added, followed by azeotropic distillation.
톨루엔이 함유한 용액을 일반식(2)의 N-시아노알킬-α-브로모-이소부티라미드에 가하고, 6-15시간동안 환류시킴이 바람직하다.Toluene-containing solution is added to N-cyanoalkyl-α-bromo-isobutyramid of formula (2) and refluxed for 6-15 hours.
본 발명을 하기 실시예로 일층 상세히 설명한다.The present invention is explained in more detail by the following examples.
[실시예 1]Example 1
N-시아노에틸 P-클로로펜옥시이소부티라미드N-cyanoethyl P-chlorophenoxyisobutyramid
냉각기와 교반기가 부착된 25ℓ반응기에 에탄올 3ℓ, 나트륨 60g 및 P-클로로펜올(1.944몰) 250g을 주입하고 1시간 교반한 후, 톨루엔 3ℓ를 가하고, 에탄올/톨루엔을 공비 증류하여 제거한 후, 톨루엔 2ℓ이상을 가하여 얻어진 N-시아노에틸 α-브로모-이소부티라미드(1.944몰) 425g을 10시간 동안 환류시키고 톨루엔 2ℓ를 증류 제거한 후, 물로 처리하여 침전시켜 분리하고, 물로 세척한 후, HC1을 가하여 중성을 만들고, 건조시키고, 디-이소프로필에테르로 재결정시킨 결과, 백색 결정성 생성물 348g(수율 : 67%)이 얻어졌는바, 융점이 71℃이었고 조성은 분자식 C13H15O2N2Cl(분자량 266.72)에 해당하였으며, 불에는 불용성이었으나 대부분의 유기용매에 가용성이었다.Into a 25 L reactor equipped with a cooler and a stirrer, 3 L of ethanol, 60 g of sodium, and 250 g of P-chlorophenol (1.944 mol) were injected and stirred for 1 hour, and then 3 L of toluene was added, and ethanol / toluene was removed by azeotropic distillation, followed by 2 L of toluene. 425 g of N-cyanoethyl α-bromo-isobutyramid (1.944 mol) obtained by adding the above was refluxed for 10 hours, 2 liters of toluene was distilled off, treated with water to precipitate, separated, washed with water, and then HC1 was purified. Neutralization, drying and recrystallization with di-isopropylether gave 348 g (yield: 67%) of white crystalline product, which had a melting point of 71 DEG C and a molecular formula of C 13 H 15 O 2 N 2. It corresponds to Cl (molecular weight 266.72), which was insoluble in fire but soluble in most organic solvents.
[실시예 2]Example 2
N-시아노에틸 P-플루오르펜옥시이소부티라미드N-cyanoethyl P-fluorophenoxyisobutyramid
실시예 1의 방법으로 제조하되, P-클로로펜올 대신에 P-플루오르펜올을 사용하여 나트륨 처리후 N-시아노에틸 α-브로모-이소부티라미드와 반응시킨 결과, 융점이 75℃이고, 조성이 분자식 C15H15O2N2F(분자량 250.2)에 해당하는 백색 결정성 생성물 (수율 67%)이 얻어졌다.Prepared by the method of Example 1, but reacted with N-cyanoethyl α-bromo-isobutyramid after sodium treatment using P-fluorophenol instead of P-chlorophenol, the melting point was 75 ° C., and the composition A white crystalline product (yield 67%) corresponding to this molecular formula C 15 H 15 O 2 N 2 F (molecular weight 250.2) was obtained.
[실시예 3]Example 3
N-시아노부틸-P-클로로펜옥시이소 부티라미드N-cyanobutyl-P-chlorophenoxyisobutyramid
실시예 1의 방법으로 제조하되, N-시아노에틸-α-브로모-이소부티라미드 대신예 N-시아노부틸-α-브로모-이소부티라미드를 사용한 결과, 융점이 88℃이고 조성이 분자식 C15H19N2O2Cl에 해당하는 백색 결정성 생성물(수율 87%)이 얻어졌다.Prepared by the method of Example 1, but using N-cyanobutyl-α-bromo-isobutyramid instead of N-cyanoethyl-α-bromo-isobutyramid, the melting point was 88 ° C. and the composition A white crystalline product (yield 87%) corresponding to molecular formula C 15 H 19 N 2 O 2 Cl was obtained.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR7700639A KR810001319B1 (en) | 1977-03-17 | 1977-03-17 | Process for the preparation of new isobutyramide derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR7700639A KR810001319B1 (en) | 1977-03-17 | 1977-03-17 | Process for the preparation of new isobutyramide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR810001319B1 true KR810001319B1 (en) | 1981-10-14 |
Family
ID=19204026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR7700639A Expired KR810001319B1 (en) | 1977-03-17 | 1977-03-17 | Process for the preparation of new isobutyramide derivatives |
Country Status (1)
| Country | Link |
|---|---|
| KR (1) | KR810001319B1 (en) |
-
1977
- 1977-03-17 KR KR7700639A patent/KR810001319B1/en not_active Expired
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HU193161B (en) | Process for preparing new n-alkyl-norscopines | |
| US4131617A (en) | Preparation of new isobutylramide derivatives | |
| KR810001319B1 (en) | Process for the preparation of new isobutyramide derivatives | |
| SU516341A3 (en) | Method for preparing substituted benzophenones | |
| IL28645A (en) | Tropine derivatives | |
| US4212804A (en) | Process for the preparation of optionally substituted 2,3-indolinediones | |
| KR870002019B1 (en) | Process for preparation of amine derivatives | |
| US4213905A (en) | Preparation of 5-aroyl-1-loweralkylpyrrole-2-acetic acid salts | |
| JPH062747B2 (en) | Process for producing 2-alkyl-4,5-dihydroxymethylimidazole | |
| EP0238305B1 (en) | 4,4-bis(4-hydroxyphenyl)cyclohexanecarboxylic acid derivatives and process for preparing same | |
| EP0738720B1 (en) | Process for producing 1-(2-chlorphenyl)-5(4H)-tetrazolinone | |
| US4031136A (en) | Process for the preparation of trans, trans-muconic acid | |
| JPS6028822B2 (en) | Method for producing 4-methylimidazole-5-carboxylic acid isopropyl ester | |
| JP2706554B2 (en) | 4-trifluoromethylaniline derivative and method for producing the same | |
| US3064004A (en) | Production of n-vinyl-2-oxazolidones | |
| SU1313856A1 (en) | Method for producing derivatives of cis- or trans-diaminodibenzoyl-dibenzo-18-crown-6 | |
| JP2824781B2 (en) | Method for producing N, N'-bis- (2-hydroxyethyl) -piperazine | |
| US4568760A (en) | Process for the preparation of lactic acid silyl esters | |
| KR810000557B1 (en) | Manufacturing Process of Chiochroman Derivatives | |
| US3676498A (en) | 1,6-bis(2-oxacyclohexyl)-hexane-1,6-diones and a process for producing them | |
| US2899429A (en) | Nitroethylenes | |
| JPS6137769A (en) | Preparation of piperidine derivative | |
| KR790001482B1 (en) | Process for preparing phenothiazin derivatives | |
| JPH0150702B2 (en) | ||
| KR950013468B1 (en) | Preparation of p-alkoxy-ñô-phenyl acrylic acid |