SU192797A1 - - Google Patents
Info
- Publication number
- SU192797A1 SU192797A1 SU1063338A SU1063338A SU192797A1 SU 192797 A1 SU192797 A1 SU 192797A1 SU 1063338 A SU1063338 A SU 1063338A SU 1063338 A SU1063338 A SU 1063338A SU 192797 A1 SU192797 A1 SU 192797A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- reaction
- mixture
- solution
- added
- water
- Prior art date
Links
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N Benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- GMPKIPWJBDOURN-UHFFFAOYSA-N Methoxyamine Chemical compound CON GMPKIPWJBDOURN-UHFFFAOYSA-N 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N Oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N [N-]=C=O Chemical compound [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- AOPRXJXHLWYPQR-UHFFFAOYSA-N 2-phenoxyacetamide Chemical compound NC(=O)COC1=CC=CC=C1 AOPRXJXHLWYPQR-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N Methyl iodide Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- HKOOXMFOFWEVGF-UHFFFAOYSA-N Phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005262 alkoxyamine group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940095076 benzaldehyde Drugs 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 229940067157 phenylhydrazine Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
Description
Насто щее изобретение относитс к способу получени неописанных в литературе Nацил-М-алкокснмочевин общей; формулы ОThe present invention relates to a process for the preparation of Nacyl-M-alkoxy-ureas common not described in the literature; formulas O
II/ORiII / ORi
R-C-NHCONR-C-NHCON
НH
где R - арилоксиацетил,where R is aryloxyacetyl,
RI - алкил взаимодействием арилоксиацетилизоцианатов с алкоксиал1инами. Полученные соединени могут найти нримеиение в качестве пестицидов.RI is an alkyl by the reaction of aryloxy-acetyl isocyanates with alkoxy 1in. The resulting compounds can be found as pesticides.
Пример 1. К суспензии 15 г феноксиацетамида в 30 мл дихлорэтана добазнли быстро 10 мл оксалилхлорида и полученную смесь нагревали иа вод ной баие 1,5 час при 60- 70°С.Example 1. A suspension of 15 g of phenoxyacetamide in 30 ml of dichloroethane was quickly added to 10 ml of oxalyl chloride and the mixture was heated with water and boil for 1.5 hours at 60–70 ° С.
При комнатной температуре удалили растворитель и последующей вакуумразгопкой получили 14,2 г (80%) феиокспапетилизоцианата . К раствору 3,2 г фенокеиацетилизоцианата в безводном бензоле добавили 0,8 г о-метилгидроксиламина . Выпавший после эиергично реакции осадок отфильтровали и иолучилп 3,4 г К-феноксиацетил-К-метоксимочевины.The solvent was removed at room temperature, and then vacuum-digging gave 14.2 g (80%) of feioxappetyl isocyanate. 0.8 g of o-methylhydroxylamine was added to a solution of 3.2 g of phenoquiaacetyl isocyanate in anhydrous benzene. The precipitate which had formed after the reaction was filtered and a 3.4 g of K-phenoxyacetyl-K-methoxyurea was obtained.
Пример 2. 90 г бензальдегида в колбе смещали 150-160 мл 20-25% раствора едкого натра и постепеино прибавили 59 г сол нокислого гидроксиламина. После полного исчезновени масла колбу охладили, полученный при этом бензантиальдоксим экстрагировали эфиром, промыли водой до пейтральпой реакции и высущили над сульфатов магни , Удалили растворитель и последующей вакуумперегонкой получили 63,3 г (60%) бензантиальдоксима с т. кип. 118-119°С/10 мм.Example 2. 90 g of benzaldehyde in the flask were displaced with 150-160 ml of 20-25% sodium hydroxide solution and gradually added 59 g of hydroxylamine hydrochloride. After complete disappearance of the oil, the flask was cooled, the benzthiandioxime thus obtained was extracted with ether, washed with water until the neutralis reaction and dried over magnesium sulphate. 118-119 ° C / 10 mm.
16 г беизантпальдоксима смешали с раствором 3 г металлического натри в спирте и 20 г йодистого метила и пОоТученную смесь пагревали в течение нескольких часов на вод ной бане с обратным холодильником. От реакционной смеси отогналн спнрт, добавнли воду и выделившийс масл ный слой о-метнл бензантиальдокснма отделили, водный раствор16 g of Beyzantpaldoxime were mixed with a solution of 3 g of metallic sodium in alcohol and 20 g of methyl iodide, and the mixture to evaporate for several hours in a water bath with reflux condenser. From the reaction mixture distilled sprint, water was added and o-methyl benzanthioledoxnm was separated off by an separated oil layer, the aqueous solution
экстрагировали эфиром. Эфирный раствор промыли щелочью дл удалени избыточного бензантиальдоксима и упарили. Полученное масло соединили с отделенным ранее маслом и перегнали. После многократных перегонокextracted with ether. The ethereal solution was washed with alkali to remove excess benzionaldexime and evaporated. The resulting oil was combined with previously separated oil and distilled. After multiple distillations
получили 10,7 г (60%) о-метилбензантиальдокснма с т. кнн. 190-192 С/760 мм, 68- 70°/10 мм. Смесь 150,5 г о-метилбеизантиальдокснма и 105,1 г фенилгидразииа нагрели в колбе дл перегонки, постепеино повыша температуру до 200°С до прекращени отгонки . После перегонкн нолучепного дистилл та получили 33,45 г (63,4%) о-метилгидроксиламина с т. кип. 48-537760 мм. 3 0,3 г о-л1ет11лгидрокси;1амина. Выпавший после энергичной реакции осадок отфильтровали и получили 2,1 г -(2,4-дихлорфеиоксиацетил ).метокси.мочевнны. Ппотмет и пбп(-г(иит предмет и 3 о о р е г L и и Сиособ получени К-ацил- -алкокеимочсвин общей формулы: 4 О |j/ORi R-С -NHCON Н где: R арилоксиацетил, Ri - алкил, отличающийс тем, что арилоксиацетилизоцианаты подвергают взаимодействию с алкоксиаминами .Received 10.7 g (60%) of o-methylbenzalanthioxnma with t. Kn. 190-192 C / 760 mm, 68-70 ° / 10 mm. A mixture of 150.5 g of o-methylbysanthio aldoxne and 105.1 g of phenylhydrazine was heated in a distillation flask, gradually increasing the temperature to 200 ° C until the distillation was stopped. After distillation of a nochem distillate, 33.45 g (63.4%) of o-methylhydroxylamine were obtained from a bale. 48-537760 mm. 3 0.3 g o-l1et11lhydroxy; 1amine. The precipitate formed after the vigorous reaction was filtered and 2.1 g of - (2,4-dichloro phyoxyacetyl) was obtained. Methoxy. Urea. Ppotmet and pbp (-g (iit subject and 3 o r e g L and the method of obtaining the K-acyl-alkokechamone of the general formula: 4 O | j / ORi R — C —NHCON H where: R characterized in that aryloxy-acetyl isocyanates are reacted with alkoxyamines.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU192797A1 true SU192797A1 (en) |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3502705A (en) * | 1967-06-26 | 1970-03-24 | Chevron Res | N-carboxyacyl-n'-hydrocarbylthio ureas |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3502705A (en) * | 1967-06-26 | 1970-03-24 | Chevron Res | N-carboxyacyl-n'-hydrocarbylthio ureas |
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