SU273200A1 - METHOD FOR OBTAINING N-ACYL-S- (O, 0-DIALKYLTIOPHOSPHORYL) -CYSTEIN ETHERS - Google Patents
METHOD FOR OBTAINING N-ACYL-S- (O, 0-DIALKYLTIOPHOSPHORYL) -CYSTEIN ETHERSInfo
- Publication number
- SU273200A1 SU273200A1 SU1276185A SU1276185A SU273200A1 SU 273200 A1 SU273200 A1 SU 273200A1 SU 1276185 A SU1276185 A SU 1276185A SU 1276185 A SU1276185 A SU 1276185A SU 273200 A1 SU273200 A1 SU 273200A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- acyl
- dialkyltiophosphoryl
- cystein
- ethers
- obtaining
- Prior art date
Links
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N o-xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- -1 dialdehyde phosphoric acids Chemical class 0.000 description 1
- ROWFPZUWPXSMPA-UHFFFAOYSA-N diethyl phosphono phosphate Chemical compound CCOP(=O)(OCC)OP(O)(O)=O ROWFPZUWPXSMPA-UHFFFAOYSA-N 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000008079 hexane Substances 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000000749 insecticidal Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002955 isolation Methods 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
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L na2so4 Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Description
Изобретение относитс к новому способу .получени не описанных эфиров N-aцил-S-(0,Oдиалкилтиофосфорил )-цистеина общей формулыThis invention relates to a novel process for the preparation of undescribed N-acyl-S- (0, Odalkylthiophosphoryl) -cysteine esters of the general formula
НОчNIGHT
;Р - S - СНг - СН - COOR; P - S - SNg - CH - COOR
RO/IIIRO / III
SNHCOR,SNHCOR,
где R, R, R - одинаковые или разные алкильные радикалы. Соединени получают взаимодействием N-ацилированных эфиров а-аминоа .криловой кислоты с диал«илдитнофосфорными кислотами в среде ксилола при те.млературе 90-95°С с .последующим выделением целевого продукта известным способом. Полученные соединени могут быть использованы в качестве инсектицидов и акарицидов.where R, R, R are the same or different alkyl radicals. The compounds are obtained by the interaction of N-acylated a-amino-acrylic acid esters with dialdehyde phosphoric acids in xylene at a temperature of 90-95 ° C with subsequent isolation of the target product in a known manner. The compounds obtained can be used as insecticides and acaricides.
Пример. К 2,05 г (0,11 моль) диэтилднтиофосфорной кислоты в 30 мл ксилола или толуола добавл ют 1,71 г (0,01 моль изопропилового эфира N-ацетил-а-аминоакриловой кислоты в 20-25 мл .ксилола или толуола и нагревают реакдионную смесь при 90-95°С при .перемещивании в течение 5-7 час. После охлаждени реа.кционную смесь нейтрализуют 5%-ным раствором соды и промывают дважды холодной водой. Органический слой сущат безводным сульфатол натри и концентрируют в вакууме.Example. To 2.05 g (0.11 mol) of diethyldiphosphoric acid in 30 ml of xylene or toluene was added 1.71 g (0.01 mol of N-acetyl-a-amino-acrylic acid isopropyl ester in 20-25 ml of xylene or toluene and heat the reaction mixture at 90–95 ° C with 5–7 hours of displacement After cooling, the reaction mixture is neutralized with 5% soda solution and washed twice with cold water.The organic layer is dissolved in anhydrous sodium sulfate and concentrated in vacuo.
Очищают многократным высаживанием из смеси эфира с гексаном при охлаждении или хроматографическим путем на колонке, наполненной силикагелем марки КСП, в системе гексан-ацетон 4 : 1 или 3 : 2. Полученный О-изопронил-К-ацетил- S-(O,O - днэтилтиофосфорил )-цистеин представл ет собой сиропообразную прозрачную жидкость соломенногоThey are purified by repeated precipitation from ether / hexane mixture with cooling or by chromatography on a column filled with silica gel of the PSC grade in the hexane-acetone system 4: 1 or 3: 2. Obtained by O-isopronyl-K-acetyl-S- (O, O - Dethylthiophosphoryl) -cysteine is a syrupy clear liquid straw
цвета; ng 1,4985; df 1,1624. Выход 1,14 г colors; ng 1.4985; df 1.1624. Yield 1.14 g
,20 ( 29,2% от теоретического, счита на изопро .пиловыйэфир- -ацетпл-а-амнноакриловой, 20 (29.2% of theoretical, counted on isopropyl ether-α-aceptl-a-amnno-acrylic
кислоты).acid).
Най.аено. %: X 3,81; 3,76; R 8,53; 8,29; S 17,75; 17,77. MR о 90,21.Nayanao. %: X 3.81; 3.76; R 8.53; 8.29; S 17.75; 17.77. MR is about 90.21.
C,.,H24NO,P.,.C,., H24NO, P.,.
Вычислено, %: N 3,91; R 8,66; S 17,94. MRo 89,99.Calculated,%: N 3.91; R 8.66; S 17.94. MRo 89.99.
Строение полученных веществ подтверждено данными элементарного анализа молекул рных рефра кций и инфракрасных спектров.The structure of the obtained substances was confirmed by the data of elementary analysis of molecular refractions and infrared spectra.
Предмет изобретени Subject invention
Способ получени эфиров N-anHn-S-(0,O25 диалкилтиофосфорил)-цистенна общей формулы 3 где R, R, R - одинаковые или разные алкильные радикалы, отличающийс тем, что N-ацилированные эфиры а-аминоакриловой кислоты подвергают взаимодействию с диал4 килдитиофосфорными кислотами в среде ксилола или толуола при температуре 90-95°С с последующим выделением целевого продукта известным способам.The method of preparing N-anHn-S- (0, O25 dialkylthiophosphoryl) -cytene esters of the general formula 3 wherein R, R, R are the same or different alkyl radicals, characterized in that the N-acylated a-amino-acrylic acid esters are reacted with dialk4 dithiophosphoric acids in the environment of xylene or toluene at a temperature of 90-95 ° C, followed by separation of the target product by known methods.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU273200A1 true SU273200A1 (en) |
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