DEP0022841DA - Process for the preparation of unsymmetrical disubstituted thioureas - Google Patents
Process for the preparation of unsymmetrical disubstituted thioureasInfo
- Publication number
- DEP0022841DA DEP0022841DA DEP0022841DA DE P0022841D A DEP0022841D A DE P0022841DA DE P0022841D A DEP0022841D A DE P0022841DA
- Authority
- DE
- Germany
- Prior art keywords
- group
- introduces
- falls
- hour
- acid
- 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
- 238000000034 method Methods 0.000 title claims description 3
- 150000003585 thioureas Chemical class 0.000 title 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 235000003599 food sweetener Nutrition 0.000 claims description 3
- 239000003765 sweetening agent Substances 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims description 2
- 235000009508 confectionery Nutrition 0.000 claims description 2
- 239000004615 ingredient Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 2
- BHMLFPOTZYRDKA-IRXDYDNUSA-N (2s)-2-[(s)-(2-iodophenoxy)-phenylmethyl]morpholine Chemical compound IC1=CC=CC=C1O[C@@H](C=1C=CC=CC=1)[C@H]1OCCNC1 BHMLFPOTZYRDKA-IRXDYDNUSA-N 0.000 claims 1
- 241001233242 Lontra Species 0.000 claims 1
- 229960000583 acetic acid Drugs 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- 239000012362 glacial acetic acid Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000008164 mustard oil Substances 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 1
- -1 amino fatty acid Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 238000005121 nitriding Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Description
Prof©sssöi? Βτβ Otto Bay®r und Br« Ernst Gaues·Prof © sssöi? Βτβ Otto Bay®r and Br «Ernst Gaues ·
es es äs iss ra t= <n» ca (£= «s ca er= s=ses es es iss ra t = <n »ca (£ =« s ca er = s = s
!©verkus©»^ den 23« Soveiaber 1948! © Verkus © »^ den 23« Soveiaber 1948
t4,t4,
ssur HersteXXimg von Sftfeteifssur HersteXXimg from Sftfeteif
* <=» «oa <ea ca G=e tos ft* <= »« Oa <ea ca G = e tos ft
Bs wurde clie ilfterrasehend© ^ea^stelluitg gemacht 9 die gern!seilten TfeioharnstoiTe der formelIt was made into a rousing © ^ ea ^ stelluitg 9 the gladly roped TfeioharnstoiTe of the formula
P-HO9. C6H4. BH. CS .ΗΗΟΗΣ. GHg. OQQHP-HO 9 . C 6 H 4 . BRA. CS .ΗΗΟΗΣ. GHg. OQQH
I)Ot5 die wasserlöslichen Saise dar-selfcen » ϊ feeSeutet Wasser«· stoff Oiler einen aliphatisehen Best - sieh diireh einen intensiv süßen miß reinen ©aachmaek aus ss β lohnen o Die Verbindungen über» treffen d®a Sohrssueker in der süSenden Wirkung im das le'hrhim«= dertfach® mä sind aus? ?erwenö-on.g als Süßstoff geeignet,,I) Ot 5 the water-soluble saise self-ce "ϊ feeSeutet Wasser" · stoff Oiler an aliphatic ingredient - see thiireh an intensely sweet mispure © aachmaek from ss β worth o The compounds over "meet the Sohrssueker in the sweetening effect in the das le'hrhim «= dertfach® mä are out? ? erwenö-on.g suitable as a sweetener ,,
Gegenstand der Eyfi&dimg sind'die zvtr Hei'stell-ang der neuen Stoffs führenden ?erfate©n,,' welch© ■=· allgemam gesprochssi = darin Ijesteherij daß man in ß^minofettsäuren» wia S-Äianin oderThe subject of Eyfi & dimg are the zvtr Hei'stell-ang of the new substance leading?
taraäiir© baw» dereüi funktiosielien Derivaten, di© p-NQgÖgH^.HH.CS-f oder daß man in p-Kitranilin am Stickstoff die Gruppe -pS.NH.CHX.ÖH^.OOQH in Form eines funktionellen Derivates einführt und gegebenenfalls ansohließend dia funk-»· tion©llen !Derivate der Säuren in die frei© Säure überführt* Bas einfachste ?erfahr©n· "besteht darin» daß man p-t-Kitropheayl·= saiaföl a:a eine ß»Äminofettsäur« 'anlagert» Es Ist ferner. iaögllehs Ten dan den ß"»ÄQiinofettsäuren entsprechenden Estern oder ihren Ii tr ilen anssnigeliesu Anschließend wird alkalisch oder sauer verseift. Ss besteht natürlich auch dl© Möglichkeits dia genann«= ten Urne et Klingen atanäohst nur mit äesi «nsubstituiea-ten Phenyl«» senfSl άητοΐιζηΐί&ιτ&,Ά und an 8 ο hl ie Send ' su nitrieren s v^öfoal aus dem entstehenden Isomerengemiacsh die p-Kltrovsrfeindmig isoliert werden muß« Sin@ andsre Ausführiangaform d©s Verfahrens ist die Högatisung tob p-Nitranilln alt dem Senf öl ©ines Esters oder Ktrila eines? ß«Aminofettsäurs·taraäiir © baw »dereüi functional derivatives, ie © p-NQgÖgH ^ .HH.CS- f or that in p-kitraniline the group -pS.NH.CHX.ÖH ^ .OOQH is introduced in the form of a functional derivative and if necessary ! ansohließend dia functional »· tion © cases transferred derivatives of the acids in the free © acid * Bas easiest experie © n *" is "that one pt-Kitropheayl · = saiaföl a: attaches a one ß" Äminofettsäur ''' It is furthermore. Iaöglleh s ten dan the esters corresponding to ß "» ÄQiinofatty acids or their Ii tr ile anssnigeliesu Then it is saponified alkaline or acidic. Ss is of course dl © possibility s dia genann "= th urn et blades atanäohst only äesi" nsubstituiea th phenyl "" senfSl άητοΐιζηΐί & ιτ &, Ά and 8 ο hl ie Send 'su nitriding s v ^ öfoal from the resulting Isomerengemiacsh the p-Kltrovsrfeindmig must be isolated «Sin @ andsre execution form of the process is the Högatisung tob p-Nitranilln old the mustard oil © ines Esters or Ktrila one? ß «amino fatty acid ·
Die «.wen Süßstoffet vor alien Siagsn derThe ".wen sweeteners t before alien Siagsn the
äußerst leieht IBelioh sad täbertreffen hierin, aueh file entsprechenden gewöhnliche» Harnstoff*©® Sin weiterer Vorteil ist ihr© nooh größer® SüBkraft*IBelioh sad excels in this, also the corresponding ordinary »urea * © ® is another advantage is your © nooh greater® sweetness *
I0) 18© feile festes teiagepiilirertes 4 senf öl verAea in βο© feilen Altehsl ©usp@aiäi®rt« Sus gibt aiae mit Überschussige^'-HatronlaOg© aikalisefe gestellt© 1WsVMg Y©» Iod Teilen ß^Alaain In 5©o feilen lasses? feiasu ami exfeitzt öi© i/2 Sttma© lang auf 6©°a Bafeei geht alias oit orange«I 0 ) 18 © feile solid teiagepiilirertes 4 mustard oil verAea in βο © files Altehsl © usp @ aiäi®rt «Sus gives aiae with excess ^ '- HatronlaOg © aikalisefe © 1 WsVMg Y ©» Iod parts ß ^ Alaain in 5 © o let filing? feiasu ami exfeitzt öi © i / 2 Sttma © long to 6 © ° a Bafeei goes alias oit orange «
alt Überschüssiger Salzsäure suo Sie kommt p ?4.rd aber "bait fest« Sufüla IsSsea im SödelSsraagalt Excess hydrochloric acid suo She comes p? 4.rd but "bait fest" Sufüla IsSsea in SödelSsraag
wird der !•»-(p^IitfOplienj'X)«=!8 (»*^»oarboxyathyl)<* thioharnstoff als aohwach gelbe Eris-tsllfiiass® aaub@s? erhalten ■und sebjßilst feel 152 · 153° ·becomes the! • "- (p ^ IitfOplienj'X)" =! 8 (»* ^» oarboxyathyl) <* thiourea as aohwach yellow Eris-tsllfiiass® aaub @ s? get ■ and sebjßilst feel 152 · 153 ° ·
Sie OgOl ^iga wäirige LSeung d@r mit Alkali (S6 B nat} gelösten ¥erbin4wag ©ehmee&t iateasYou OgOl ^ iga aqueous solution d @ r with alkali (S 6 B nat} dissolved ¥ erbin4wag © ehmee & t iateas
18© OiQiIe 4»KitrophexQrl8ejaf ei w@rd©n mit18 © OiQiIe 4 »KitrophexQrl8ejaf ei w @ rd © n with
propionitril hinau· Dalsei erwärsnt siols der Äasatg; alles gelt fill0 Jmrrn Zeit in Iös«ng? worauf.'ä©r gabildat® SMohamstoff als dicke gelbe KristaXlfsa®3@ ausfällt« Maa Isaaa die atsgeaaugtt Yerbindimg aurch Uffikristallisieraa aus Bigesei Ip © 153 - -155°. Ausbeute 9© f'opropionitrile out · Dalsei warms up siols of Aasatg; all fill gelt ng 0 Jmrrn time's PSI "? what.'ä © r gabildat® SMohamstoff precipitates as thick yellow KristaXlfsa®3 @ «Maa Isaaa die atsgeaaugtt Yerbindimg aurch Uffikristallisieraa from Bigesei Ip © 153 - -155 °. Yield 9 © f'o
Ban gleichen Körper erhält man fireeeh molaren Mengen 4-Iitraailia «ad B^CyaaatliyisenttSiWith the same body one obtains fireeeh molar quantities 4-Iitraailia "ad B ^ CyaaatliyisenttSi
ZurTo the
thioharnstoffs löst man 15 Seile Ib 1©© Seilen to bei 7o° land läßt 4 Stunden bei 5o° stehen. Beim ÄMlhlsa kristallieiert dl© Carbonaäure ausa Sie sehfflilsi: 1^1 152 - 1539 iat identiseh alt der la Beispiel 1 b©s©hri@t>©sa©& fthiourea is loosened 15 ropes Ib 1 © © ropes to at 70 ° land is left to stand for 4 hours at 50 °. In the case of ÄMlhlsa, the carbonic acid crystallizes from a sehfflilsi: 1 ^ 1 152 - 153 9 iat identical to the example 1 b © s © hri @ t> © sa © & f
5e) Aus S^Alsaiii^Sttijfleste^^eliio^Iiyfi^at atall'fe m sich sit fM^pIiosgea eis© e\i%@wg®®iimiä® X^äosss^iSl fc.e2?9 Sas 1 ms* zwiaeliea 9o - 9^° ©ladet.5e) From S ^ Alsaiii ^ Sttijfleste ^^ eliio ^ Iiyfi ^ at atall'fe m sich sit fM ^ pIiosgea eis © e \ i% @ wg®®iimiä® X ^ äosss ^ iSl fc.e2? 9 Sas 1 ms * zwiaeliea 9o - 9 ^ ° © ladet.
Claims (1)
echmeckea intenaif süß mit aehwaeh bitterem laehgeschiaaek« i fabric sahmilst hot 185 ° »Saina
echmeckea intenaif sweet with aehwaeh bitter laehgeschiaaek «
Family
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