CS214360B1 - Novel 0-/2-chlorethyl/0-alkyl/n-alkylamido/esters of chlorthiophophoric acid and method production the same - Google Patents
Novel 0-/2-chlorethyl/0-alkyl/n-alkylamido/esters of chlorthiophophoric acid and method production the same Download PDFInfo
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- CS214360B1 CS214360B1 CS841480A CS841480A CS214360B1 CS 214360 B1 CS214360 B1 CS 214360B1 CS 841480 A CS841480 A CS 841480A CS 841480 A CS841480 A CS 841480A CS 214360 B1 CS214360 B1 CS 214360B1
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- Prior art keywords
- chloroethyl
- toluene
- formula
- analysis
- alkyl
- Prior art date
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- 150000002148 esters Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000002253 acid Substances 0.000 title 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 45
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 18
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 13
- 125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 12
- 229910052698 phosphorus Inorganic materials 0.000 claims description 12
- 238000004458 analytical method Methods 0.000 claims description 9
- 238000003756 stirring Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- -1 O- (2-Chloroethyl) N-isobutylamidochlorothiophosphate Chemical compound 0.000 claims description 5
- 238000004821 distillation Methods 0.000 claims description 5
- 239000011541 reaction mixture Substances 0.000 claims description 5
- SZIFAVKTNFCBPC-UHFFFAOYSA-N 2-chloroethanol Chemical compound OCCCl SZIFAVKTNFCBPC-UHFFFAOYSA-N 0.000 claims description 4
- KDSNLYIMUZNERS-UHFFFAOYSA-N 2-methylpropanamine Chemical compound CC(C)CN KDSNLYIMUZNERS-UHFFFAOYSA-N 0.000 claims description 4
- GBVFVGPEWKNSBI-UHFFFAOYSA-N dichloro-(2-chloroethoxy)-sulfanylidene-lambda5-phosphane Chemical compound P(OCCCl)(Cl)(Cl)=S GBVFVGPEWKNSBI-UHFFFAOYSA-N 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims description 2
- 238000004566 IR spectroscopy Methods 0.000 claims description 2
- 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 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 150000001412 amines Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 229910001628 calcium chloride Inorganic materials 0.000 claims description 2
- 239000001110 calcium chloride Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical compound OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 claims 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- CBMSDILKECEMOT-UHFFFAOYSA-N potassium;2-methylpropan-1-olate Chemical compound [K+].CC(C)C[O-] CBMSDILKECEMOT-UHFFFAOYSA-N 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 description 1
Description
Predmetom vynálezu sú nové 0-/2-chlóretyl/0-alkyl/N-alkylamido/ estery kyseliny chlórtiofosforečnej a sposob ich přípravy. Uvedené zlúčeniny je možné použit' ako medziprodukty pri ^syntéze esterov kyseliny tiofosforečnej.The present invention relates to novel O- (2-chloroethyl) O-alkyl (N-alkylamido) chlorothiophosphoric esters and processes for their preparation. These compounds can be used as intermediates in the synthesis of thiophosphoric acid esters.
Z literatúry sú známe 0-/2-fluóretyl/0-etyl ester kyseliny chlórtiofosforečnej, ktorý sa připravuje z 0-/2-fluóretyl/dichlórtiofosfátu a etylalkoholu za přítomnosti trietylamínu a 0-/2-fluóretyl/-metyl chlórtiofosfonát, ktorý sa připravuje reakciou metyl dichlórfosfónovej kyseliny 2-fluóretanolu v přítomnosti trietylamínu /2.obšč.chim. 29, 1671 /1959//. Taktiež sú známe O-/chlórallyl/S-alkyl, aryl, aralkylchlórtiofosfáty /Pat. SSSR 566.847/.Chlorothiophosphoric acid O- (2-fluoroethyl) O -ethyl ester, which is prepared from O- (2-fluoroethyl) dichlorothiophosphate and ethyl alcohol in the presence of triethylamine and O- (2-fluoroethyl) methyl chlorothiophosphonate, is prepared from the literature by the reaction of methyl dichlorophosphonic acid 2-fluoroethanol in the presence of triethylamine (2 nd). 29, 1671 (1959). O- (chloroallyl) -S-alkyl, aryl, aralkylchlorothiophosphates (Pat) are also known. USSR 566,847 /.
Teraz sa zlstlli nové 0-/2-chlótetyl/0-alkyl/N-alkylamido/ estery kyseliny chlórtiofosforečnej všeobecného vzorca IThe novel O- (2-chloroethyl) O-alkyl (N-alkylamido) chlorothiophosphoric esters of formula I
v ktorom R1 znamená alkyl s 1 až 4 atómami uhlíka, X znamená kyslík alebo -NH skupinu.wherein R 1 is C 1 -C 4 alkyl, X is oxygen or -NH.
Súčasne sa zlstil sposob přípravy zlúčenín všeobecného vzorca I reakciou O-/2-chlóretyl/ /dichlórtiofosfátu vzorce IIAt the same time, the process for the preparation of the compounds of the formula I by reaction of O- (2-chloroethyl) -dichlorothiophosphate of the formula II
214 360214 360
214 360214 360
Cl - CH2 Cl - CH 2
/11/ s alkalickým alkoholátom všeobecného vzorce III(11) with an alkali alcoholate of formula III
R1 - OM /111/ v ktorom R1 má už uvedný význam, M znamená alkalický kov ako je sodík, draslík, alebo s amínom všeobecného vzorca IVR 1 - OM / 111 / in which R 1 is as instructions listed above, M is an alkali metal such as sodium, potassium, or with an amine of formula IV
R1 - NH2 /IV/ v ktorom R1 má už uvedený význam v prostředí inertného organického riedidla pri teplote -5 až 25 °C.R 1 - NH 2 (IV) wherein R 1 is as previously defined in an inert organic diluent at -5 to 25 ° C.
Zlúčeniny pódia vynálezu vzorca I možno tiež pripraviť reakciou zlúfeniny všeobecného vzorca VCompounds of the invention of formula I may also be prepared by reaction of a compound of formula V
s 2-chlóretanolom za přítomnosti činidla viažúceho vznikajjúci chlorovodík ako je trietylamín, pyridin v prostředí inertného organického riedidla pri teplote O až 25 °C.with 2-chloroethanol in the presence of a hydrogen chloride-forming agent such as triethylamine, pyridine in an inert organic diluent at 0-25 ° C.
Následujďce příklady bližšie osvetíujú ale neobmedzujú nové O-/2-chlóretyl/O-alkyl/N-alkylamido/ estery kyseliny chlórtiofosforečnej a sposob ich přípravy.The following examples illustrate but do not limit the novel O- (2-chloroethyl) O-alkyl (N-alkylamido) chlorothiophosphoric esters and methods for their preparation.
Příklad 1Example 1
0-/2-chlóretyl/0-izobutylchlórtiofosfát0- / 2-chloroethyl / 0-izobutylchlórtiofosfát
K 1 molu 0-/2-chlóretyl/dichlórtiofosfátu rozpuštěného v 600 ml toluénu sa za miešania přidalo v priebehu 120 min. 1,05 molu izobutylátu draselného, rozpuštěného v 100 ml izobutanolu a v 150 ml toluénu, pri teplote O až 8 °C. Po přidaní sa pokračovalo v miešaní ešte 3 hodiny bez chladiacej lázně. Potom sa reakčná zmes premyla 3 x 500 ml vody, vysušila sa a za zníženého tlaku sa oddestiloval toluén s izobutanolom. Destilačný zvyšok sa predestiloval za zníženého tlaku. Získalo sa: 239,5 .g bezfarebnej kvápaliny o t.v. 75-77 °C/26,7Pa n20 . χ,49χ3 a zloženia:To 1 mole of O- (2-chloroethyl) dichlorothiophosphate dissolved in 600 mL of toluene was added over 120 min with stirring. 1.05 mol of potassium isobutylate, dissolved in 100 ml of isobutanol and 150 ml of toluene, at 0 to 8 ° C. After the addition, stirring was continued for 3 hours without cooling bath. Then, the reaction mixture was washed with water (3 x 500 ml), dried and toluene with isobutanol distilled off under reduced pressure. The distillation residue was distilled under reduced pressure. Yield: 239.5 g of a colorless liquid of 75-77 ° C / 26.7 Pa n 20. χ, 49χ3 and composition:
Analýza pre CgH^Cl^PS Vyp.: 12,34 % P 12,77 % S 28,24 S Cl /m.h. 251,02/ Zist.: 12,11 %P 13,08 % S 28,48 % Cl.Analysis for C 8 H 11 Cl 2 PS Calc .: 12.34% P 12.77% S 28.24 S Cl / m.h. Found: 12.11% P 13.08% S 28.48% Cl.
Struktúra zlúčeniny bola potvrdená IC spektroskopidou.The structure of the compound was confirmed by IC spectroscopy.
Ič spektrá v CC14 = V/P S/ s 695 cm-1 ^/Cl-C / : 582 cí1 ^/P-O-C/ : 895>970;985;1055;1100 cm“1.IR spectra of CC1 4 = W / PS / 695 cm s -1 ^ / C-C / 582 CI 1 ^ / POC / 895> 970, 985, 1055, 1100 cm '1.
Podobným postupom boli připravené zlúčeniny:The following compounds were prepared in a similar manner:
O/2-chlóretyl/O-metylchlóreiofosfát n20 = 1,5037 t.v. = 65 °C /13,4 PaO / 2-chloroethyl / O-methylchlorophosphate n 20 = 1.5037 tt = 65 ° C / 13.4 Pa
DD
214 360214 360
Analýza pre C^Cl^PS Vvp.: 14,82 % P 15,34 % S 33,93% Cl, /m.h. = 208,97/ Zist.j 14,42%P 15,98 % S 33,44 % Cl.Analysis for C ^ Cl Cl ^ ^ PS PS Vp: 14.82% P 15.34% S 33.93% Cl, m / h. = 208.97 / found 14.42% P 15.98% S 33.44% Cl.
Q-/2-chlóretvl/0-etylchlórtiofosfát n^0 = 1,5002 t.v. : 80 - 82 °C/121 PaQ- (2-Chloroethyl) -O-ethylchlorothiophosphate n = 0 = 1.5002 tv: 80 - 82 ° C / 121 Pa
Analýza pre C4HgCl2O2PS Vyp.: 31,80 % Cl 13,88 % P 14,31 % S, /m.h.-- 222;98/Analysis for C 4 H 9 Cl 2 O 2 PS Calc .: 31.80% Cl 13.88% P 14.31% S, / mh-- 222; 98 /
Zist.: 31,66 % Cl 14,10 % P 14, 62 % SFound: 31.66% Cl 14.10% P 14, 62% S
0-/2-chlóretyl/0-izo-propylchlórtiofosfát n20 » 1,4962 t.v. : 75 °C /53,4 Pa0- (2-chloroethyl) O-iso-propylchlorothiophosphate n 20 »1.4962 t: 75 ° C / 53.4 Pa
Analýza pre C5HUC12O2PS Vyp.: 29,91 % Cl 13,06 % P 13,49 % S , /m.h. '» 236,99/Analysis for C 5 H U Cl 2 O 2 PS Calc .: 29.91% Cl 13.06% P 13.49% S, / mh »» 236.99 /
Zist.: 30,16 % Cl 13,22 % P 13, 62 % S.Found: 30.16% Cl 13.22% P 13, 62% S.
Příklad 2Example 2
0-/2-chlóretyl/0-izobutylchlórtiofosfát0- / 2-chloroethyl / 0-izobutylchlórtiofosfát
K 1 molu O-izobutyldichlórtiofosfátu rozpuštěného v 600 ml v toluénu sa za miešania pri teplote 5 až 10 °C přidalo 1ÍO5 molu 2-chlóretanolu a 1,05 molu trietylamínu.Po přidaní oboch látok sa pokračovalo v miešaní 8 hodin pri teplote 40 °C. Potom sa reakčná zmes ochladila, premyla 3 x 500 ml vody. Toluénový roztok sa vysušil a toluén sa oddestiloval za zníženého tlaku. Destilačný zvvšok sa nredestiloval za zníženého tlaku. Získala sa zlúčenina o t.v. - 75-77 °C/26,7 Pa, ktorá je identická so zltíčeninou v příklade 1.To 1 mole of O-isobutyldichlorothiophosphate dissolved in 600 ml in toluene was added 10 mole of 2-chloroethanol and 1.05 mole of triethylamine while stirring at 5-10 ° C. After the addition of both substances, stirring was continued at 40 ° C for 8 hours. . Then the reaction mixture was cooled, washed with 3 x 500 mL water. The toluene solution was dried and the toluene was distilled off under reduced pressure. The distillation residue was not distilled under reduced pressure. A compound of b.p. - 75-77 ° C / 26.7 Pa, which is identical to the compound of Example 1.
Příklad 3Example 3
0-/2-chlóretyl/N-izobutylamldochlórtlofosfát0- / 2-chloroethyl / N izobutylamldochlórtlofosfát
K 0,5 molu 0-/2-chlóretyl/dichlórtiofosfátu v 300 ml toluénu sa za miešania přidalo 1,05 molu izobutylamínu v 100 ml toluénu pri teplote - 6 až 0 °C počas 90 minút. Po přidaní sa reakčná zmes miešala 2 hodiny bez lázně, potom sa premyla 3 x 300 ml vody, vysušila sa bezv. chloridom vápenatým. Toluén sa oddestiloval za zníženého tlaku a destilačný zvyšok sa predestiloval za vákua. Získalo sa 33, 3 g bezfarebnej kvapaliny t.v. 108 - 110 °C/26,7 Pa n20 « 1,5130To 0.5 mole of O- (2-chloroethyl) dichlorothiophosphate in 300 mL of toluene was added with stirring 1.05 mole of isobutylamine in 100 mL of toluene at -6 to 0 ° C for 90 minutes. After the addition, the reaction mixture was stirred for 2 hours without bath, then washed with 3 x 300 ml of water, dried without addition of water. calcium chloride. Toluene was distilled off under reduced pressure and the distillation residue was distilled under vacuum. 33.3 g of a colorless liquid were obtained at 108-110 ° C / 26.7 Pa n 20 «1.5130
DD
Analýza pre: CgH^Cl^JOPS : Vyp.: 28,35 % Cl 12,38 % P Zist.: 28,78 % Cl 12,82 % P 13, 01 % S. štruktúra zlúčeniny bola potvrdená IČ spektroskópiou.Analysis for: C 8 H 11 Cl 2 JOPS: Calc .: 28.35% Cl 12.38% P Found: 28.78% Cl 12.82% P 13.01% S. The structure of the compound was confirmed by IR spectroscopy.
12,82 % S, /m.h.12.82% S, m / h.
250,12/250.12 /
Ič spektrá v CC14 Spectrum in CC1 4
7P S/ J/C - Cl/ ýp-o-c/ % - H /7P S / J / C - Cl / pp-oc /% - H /
665 a 692 cm665 and 692 cm
570 cm570 cm
887; 955;972:1O5O a 1105 cm'887; 955; 972: 1050 and 1105 cm -1
3430 cm3430 cm
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS841480A CS214360B1 (en) | 1980-12-03 | 1980-12-03 | Novel 0-/2-chlorethyl/0-alkyl/n-alkylamido/esters of chlorthiophophoric acid and method production the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS841480A CS214360B1 (en) | 1980-12-03 | 1980-12-03 | Novel 0-/2-chlorethyl/0-alkyl/n-alkylamido/esters of chlorthiophophoric acid and method production the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS214360B1 true CS214360B1 (en) | 1982-04-09 |
Family
ID=5434650
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS841480A CS214360B1 (en) | 1980-12-03 | 1980-12-03 | Novel 0-/2-chlorethyl/0-alkyl/n-alkylamido/esters of chlorthiophophoric acid and method production the same |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS214360B1 (en) |
-
1980
- 1980-12-03 CS CS841480A patent/CS214360B1/en unknown
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