DEP0040702DA - Process for the preparation of new acylating agents. - Google Patents

Description

CIBA AKTIENGESELLSCHAFT, BASEL (SWITZERLAND)

2 2 acrii in the

Germany .

Process for the preparation of new acylating agents.

S ^r -J mir-ijs (· βί.ν, πύ & \ κ, lace. Ban ^ «srbvollo Acj'lIi3; -: n: <. Ngsmitt @ I

, .COOH
EC - SO-H

'«Or ' ..D. Σ © ir * Ohle «: ¹ " odc *: · Hroaat-cc) bs Licufcet _i : lu Gsgönwart θ Inas tJöb ©! ⁵ - =

ßrli ', .. p.of. ε λ ^- A'i.-r •, ■ ^ -rlr ¹ :? ::,: - '·>:: ^; ⁷ .i. eiru ^ a ^ o ^ tisf-hc-n Swli ⁱ oma Sm ^a © ~

halide o-rlij? tox ^ ugfniGioe mifc Pitosgea yshaKcIeIt "

Ala Sö .uvCD öfop CfDS-Ufiteit ¹ Gyic] ®].! Formula kousoasm when present OOH _t -

geö ^ öna Y @ rf a'ii.r- & n Jxi ^, ov £ 3 £ .ai ^ & tu ⁱ ®ij-ali ^> ons ^! } i .UA '© (HC' --- PCL · H} until vop-

^ COOH

suf-xv ;? jf? e 01 ?! ore α: υ 3 p: z &vz-QSu'iJ ~ oriv.s.uz '? {" ^y IO ~ ™ * - ~ 80.,. E} in Befcraeht" This ©. ^ Cl ^y

EnX ο- n® s & .Igs 'ö.n>: · 3 πι j .Ifca :. 2 üur - && $ ± ml t, r <k * \ mxb. 31 & Isoseii 5 iah a "B _c through Ifc ·; .itamig ßor- © \ ν £ 0ρΓ6θ1 · 'ν ,? Όοη PxüoßosesÄi.P.KM.v ,!'«! ». with SefctrefsIti ^l ioxyd

Alo λ * ,: ·· οϊγι? Λ • ".. 's ^ J ^- -o • -' ■ 'IJ:'*; Λ.ϋ ,; Vr.o: ':>' lxa.i » '' :, T.ü.v >, IfI >! I \ rc5 ^{;! -} h '3nflst »an at the vcrligJO'ö ^ sB. Vea ⁱ Arahrsa tJ.t, Yortoil © Ssfsafc built utas easily accessible« 11'; -. ! -; DWfciuüuag:; »! ,, ·:" 02 · ;: ^{υ .η -} £ "'3 .1ίί & ^ äu ^ üülilojiiiic roxi sulfonic acids öer AfL ·? ·: I." · ¹ ? ·. i * d 'y Λ: "S ₄ Bi, _r.? cö.r λ '.! f ο:? ^?, ^ .alc ^ i ή ixier p-Toluolsulf oa «

According to the present proceedings: «? Production of acylation I ⁴ Iingsmitteln vird la Gegeawasrfe worked a "tertiary Bage. Here bsispi lö © ¥ elee Ts can _j ⁹ Imethylairiin, triethylamine _# H-Biethyl- morpholine or preferably pyridine are used as bases. The tertiary © base must at present © »ν οι Γι, b-voc '." Fliurr available BSIA _is like _s, h "it rnuBE rasfar ^ _oa' floi uu - h * C _ c ^r - * u ils to Absätt FINISH all required in Reaktioaageniisoh present Säur®gruppen is "Bi © tertiary Baso can be referred to in the present method receives borrowed AoyllerungemitteIn sees only as a means but säürebindendes AUOH as a solvent for that too. acyllerenden'Stoff © serve,

An expedient embodiment of the process consists in introducing the haloacetic sulfonic acid la the tertiary base and then adding the Saursnaiogeaid (a “B _s p -toluoisulfonic acid world) to all of _{the saanlien with a slightly increased portion i} S ₀ B _{0 at 30-40 °,} or gaseous phosgene © Inleitet.

A particularly valuable treatment is obtained if the compound obtained after the above-mentioned very even white with silting up of pyridine as tertiary base is still stronger than tertiary base than pyridine, e.g. hinsujf Cgt «So you can, for example, Ohloressigsäurenulionrsävr-: with pyridine. vorni: Uiö'ir, n, daan the arosate Isohe Sulfonsäur®- heioü - '^. ü nu-jcbo- o * :: * · .-: · »- · £ rr v ' i ^r . :: ·· *: · Sc · r and seßlleßslien add triethylamine.

A '. "T.""... fc ~ ν it ' i. / Ir, irIt · c ¥ 0b Pyi ^s Ictia and Ia Qsgensmrt νoe Trlaethylamin. Or Tffiathylaaia _t . 'Bo is for fi @ n smooth Yei ^j Iauf since Eeaktloa generally © la Susats Elaea inert organic solvent vim Bsazöl, Chloybenzol _fi o-Dlehlorhenzol, 1,2,4 · - Trlohlorbensol, Iitrobeasol _i Dloxan © advantageous to So you can, for example, the bromine or CMoressigsäuresulfonsäure old one.. ύ & τ bring out the solvents mentioned in aaaaisn, add triethylamine and enter the acid halide or initiate Plxosgea.

Instead of the free chlorine or Broiaei3Sigaäup®3'ulfonic = · acid, isan b @ in the TOPltageKdeii? Ss «f e & ran sueh 'ton οInora AlkalIsals run out of these connections.

As soon as the present process is obtained, Acsjll® · »yiiBgsaiittel Bind Qira _a they contain © ia halide of an acid © ä®r

HC - 30, H

in which X denotes a chlorine or brostatoa, as well as an excess of a tertiary base. There is an assumption that the acid halides contained in these acylation agents generally only contain the -COOH group in the -OO-halogen group, e.g. the -CO - ⁱ Cl,

Is _il converted during "Ii ©. to see © bsnfalls on? Formation of an acid halide solution capable "SO ^ H group is not converted into the group " • SOj ₃ - halogen.

This © new Aoylieruagsmlttel can aur Aoyllerung & @ τ different ^ SS-Grisppen or »OH« € * ruppen ® nt halt sas® η Verhi ')'? '"Rfii ^"? Ι3 # β. · Bi »As ^ Mer wig ! Bit ßi ^ pien means succeeds sllge * · Hf-J 2 <· »h '^ ifiat« Of particular importance is the stock that

rait - * ή .eof »o » Λ · "ί · .γ ·., rain, ablast in Fallsn =, tro slofc Aejll © -

', ^r j Itoi * r: i ..-' - \ "· ssitsii AajIgrappe In a © Mcnosojlr , i ut, '» V 3'"Ei -CO ~ S) de.? Pall lot, oil acylation in general

^ 3 '1 rj'. '. ^ ■ t: / ",. ¹ ". if; L Ί ^ '^ - ο Aoylle- ^ imgi »-

i'ji-Ir »"

> ~ 0E

-CO-IE-AfjI

θ at halts a * 03 ? iB an as. dsn cSurefa ValeasstslGhe b © a®Iehnetea Stiellea with the ßeasolköpß koadsaslobten i'iügf örmigan reads «, Bai ä®s? DIaoyl ie Siffig äi @ 3®2 * Azof syfeatoffe with <3s near the 1 ; ^ oj c-- · γ * 1 . 'ο <> _i * U .a Af z "~ rj ic jMX * ^. τ ι h ' OEa

At Oiags ⁵ UppIex ⁵ UBg

i '/ ->. ". y ^, - o OO-HC

CO

^r : "" sl '"' - f Ui '' ^ c- r-"'I ^r -T · Ir : - ^- jl9' ίΙκΓΌί.ί p: tr _: ^ fC »r ' ^- >« ^- ° H ^ st tine? λ

holdsIishen Λ?. ·. . .j "τ ,,; • i '■ c 3 *% r _t .. ι: • c, 1. » > i " O,>r't / ν -

ι 'r- "' Λ. ~> V. V 'J.Zrr ^r : ι' ^Λ , " · - ~ ■, - 'V ™ "- ι ■» * v \ - V ⁵ Il <V . _rJ f "v :: Ci '. L «.- V <c" vVv ., ^{No, 1} , ν sVv

3 ν ¹ . γ- "v. ! -γ -," ■ <"_ Π", '- ^, ^Ί ·'"Tfj V ·· ι, 0 γ,

i ι. ■ ^f VispL '... ■' Vv -> ~ νρ Ij ¹ J ¹ * 'Η' ·: τ:, j ι. · I. ·, 'L> -: <__'"v / aJ η

: C- ii «" Xii,: · ¹ "ν ^ r *""' ^r jf /, e * ^ _t O _{l t} ; f ^ ν ^ ^s > ru

Wfx JäVü ü ».Ρ> V, ο« lVL „f VT» "ZV- 't""!" Ti , uJ ι 1 i -i. s> - / O ^- : '- j V.lcr' Γ ι -> _Λ IUltI C, _fc , «- - · κ t \>■" ¹ '' V ¹ '-1 .I _v , \

ⁱ ac ν «.aefe © ii> v V Vv _ j-jw. t-Jia ^oi V '* · vj : Γ ^u i . "c"" _t So L ~« i ^ I j.'"RJ" 2 riv 'JVv ν »c _it JwIT > oi ivv ^ agy-

wä .rt .1 "« ii «, '·» 3 ic "i Ci'" 0 « j {- rü" w , .is' Gt to »e-sulf on- Sv- - v *«. V>. »- r 'O'C ¹ ·' ^r i ~ t'iiJS""ί * cn © f '& F pyridine)

> γ: ί, · ί; \. > Mr u >'ζ-ξ"" _ oij ν;. ι ·, μ _r . : «; ι f "u" g - ', foaBäur © - =

* '. "· * Rrc ■" i. i './ρ: lt'" ¹ oj- ¹ ν 'siv;-> _u and oil®

fsi;, ir?:, aoäiir '3 with Gv.-mi ^T a: vbcitr.-i'f clivro * T ^ - O ¹ VTrr. v .: νν .ι vi

r -vi " w ν fi'- vV'V" - oior 50 .Igr ε u ^: -α- L < λ "1- π t. pV ~ f ^j i.oom

evtloiVBiu siinlvasaxi beat.

ι., rcr ^ / i «^ ''•" • "• '. •.,', 'V -Iy -...!' · ...- ■ · Υ", Y -1 'ν y Y ; c

• c:. · 'Y ^- V-. f;. · - ^r J 1. ι · "■ f " ^: Yrvvv- "· Γ- .J ei;. ·" Jr ί ί- ^:. ,

* Y i. - '> JJv. ϊ ·. . ·,, -'-... it Y:: ·,;: ■ * .ν. λ - ού, ίν r ν lv; l, - :; τϊόίϊ

, ν .ϊίίΛ ί -ei ', -, "Iif _t ι ¹ ''"' •• V _jl ; YY νν '/:1η;.· Aasoen

Ii. -y- "C ^r νίν, ^r Y ',»: Yv.-. ■ ". ■ ".Ο *, λ ο ::.; ·. · J, ν YY.-vJ rl p ;;>n". us-

cvv ^ ViTt-JC »'Vf'VTi -. /. - _ V ^ Y ⁵ v ? Ν JJ - v ΐ? "·" *.

^ <v "" - ^s · _,, «'' s , Πνϊ-" -Iii. λ-ill YTVVVt Γ ί ^! .5ρ

7 ίΥ ■ 'JiVr ^c ; *; - ~ ^τ '. "■ '>Jr'v el υ t' ν. Ν ν Y. · -Jv ϊ. ) Y .. 5, YrvY, η ί.. J ν." Each V ₁ J: - ;, ", ν τ -.": 1 ". ^Γ '''ν γ ·.!, YiY _r '·" - '.. ί "': υ;"<.. ν Ji t'cs, iv; v α-- ".« I ·· ?. ' i -J \ Ί Λο? τν ..: '· Λ t-: ί Ji ¹ ν ;; - λ "ί ,. ^; vyc-'Λ rYvJ> .ν YiYc .ν ,, · ' ·: / · · · .. * "i _; >> · FQl ^ n _e

-: ννν, JrY

^:: V ^r .YJ ν · JvY. J. ··;.!. : TVV ·. :: /..- .JiV-TiW, // <Ύ £ .V.CVT- ', Vi.Oll Y ...', ";. · - - * - /". · ■ ' ..- t- "V Γν V Y- · Vvvi ?: IV. Ic ν>' α ·," L ^ de -.-' y

j-vXi ^: - ^ι "^ ί · '- · ■ ^''^) ^ ^r " J -' ^t ^ '· ^: ' ^: ίΰ C-ν-: VVV-VT-τ r " ^f -. λ, .'λ , ic-J. ^ ν.νΓ ^ Ι-

«■ ϊΤ- · V -J;: · ' - · ί " J ^; J ' GJlv,.:.;. L; .v'io \: - Jiv-, v .; VV-.C '- ι .ν. *.: - J ..: fYv-jiiv : V '' ·. ". 'J' -. V ⁱ Jvv -'.- -, ., J '■ · ■■■■' _ '' ν- ( . 1 .. v.-: ^"F ^ TJ ₁ CtalltJi-Si? * J - · _£;; .V js-i · ί-, 7ί ··..

- ·· ■ ·· 'ν' ^t J '' vir 'J · ⁰ ' ιC ^Γ \ V ^ ^s -

- '"■'., ''" .. · .. 'Ί -τ .- "Λ. ■ Jt _r ν -TVi ^ i

ί: ' ..' iJf.c: Γ s \; - · < _: "" t it j "- '' v. ■" I, ', · * ·: · & γ ·, - ^ ofe ι? - « : -Λ LVSAVs-Zii _i , ί "· rc, - ·, · <Υ _, -.-J: · \; ■ 'V ί · ->. 4ο.ι. <·. *, Η .ο λ- ·;. <Ί · Υ4 tu taiS

I, -O = -Co .. * L »/ rv. ί «\""\;, ··. ·, j> j ν i.C't-L BO'.L'üIe? "iui» -ve / λ £ ί> Min ₀

ants SVm ·. ·, - · '. e ι. ''<' ΓλκκΙ. · Ί * ■ τΓΐ -ϊι \ γ ΐ. ^ '■ • .-. I- jt .nC dr ^ -a Ib

λ ¹ >"!.'_." γ \ < ? - "i'i.-'- -, - a -λ υ ί ¹ ·;„ »:. ο ϊγ ΛΛ-.ϊ .!" our ,, jnt3? .1. © r- ~

ΐτΊ ''"·'.Ci Ku' J - ί '-' ·: νν„ '., τ; ,, ^ Tfiji ν «.' · ■ · Wj r.rüÄ -iuM" '-h.:^i ~ '} C : .ί, tdr Λ> .η "<>-.''">' Γ Vifv-f- m ^{f /} t f. J ζ: " λ \ ϊ;:, λ ΎϋίνΓ Via .; ' - iiv.sg®-

¹ⁱ ViX · » " ■ i "-7>; -. ί · / V '·· V - ^ o *. · \'<~ jr », ^ ·;. £ <>; ji: Xyo! c I; osk ™ I: ¹ c π'ΐ ^"! LI · R.- Ί, ιν · π * • '" ■ i τΛ υ, i ΐ "" ίϊ'υ γ * ^c: tv * j dca

? ·. · L'- ' ^r "' ^: j · ' ⁷ '"'' - · ' ^: '"'·' - ' ⁱ '''' ^r ^"*' ^: " ^Γ ί v.. • ji '-.jd .t \ η j:. ". *" n _n l \ ;; / i; t. e · «(. * ·.? v * L -« ^ j. ".: 2 ⁱ Y ₁ - • ^ '. • f.; _{.. c t} ü.' unve: '' • Su- = f; ⁴ υ "Όΐΐ J ^ i; .- * - · ..: '«.'"'· ■ ^. N ^ u ei.a:>'} <■) \ Oi>y>: i Is ⁴ « d : · "·: ^ D ge

jj 'f -ti * "ö r <i ;. * _ ν <;. ·· ¹ r;,: ^ i ·:; ϋ., ί · ί-r. mi ■ l ^ /. I'r & ΐ ι ".7Λ · afC? .u ümi 7 -u3kiv. .ι: Ί · '. ^r J - · 'C [y ^' · ~ \ ι \ .? _ή <η ··· '··· ^f f ^ ic- :,,' rr-j if a »fiiöL In

jit ·. "<::> ι ·· lc ~ <j ~ '"c' j '; r ... ^ ti / I.- " -a ^ ^r I' - * ,. /.vi'i "- *. r '-.itlo ^ o ^ igan

IMi ι /. « ^F J dc. .τ-- · f, * h: j'K r >·;;.·; ? ^! "ii't ·";.;. ^ »." L 1: 9. SJ Iwp _l OUh TOP.

Ώ 'ι- f "''ϋj' _t " ^γ ·; rs '"""s U J, ^: i'-a- <; rib ' ^: jO" ΤολχΏ, ί-

Li "'- , <Λ' \. ', ·>',>'}"' T 'Λ *, λ " ^Γ ". ".V ^ w .'l,' UCULJOVSt _c ,

Ι> οε ΐ "θ; Γπ :: · ίκ · '' χ · Ί ν · ν « Ρ3 ^ cvr., - _rri -. _R ■ ^ "- ^ c ··. ' γ · \ ■ ν "π- ?? - bIrrt, IiB-Qh

Mt /

.1 ^; · I, - » ^f I ⁷ c * i ^ fr ;. ' ir :, γ, j; «- ::;, ο ,, r - ^? -.« '• c -, Dc ^f · ev? C Λ * ιλϊ Λ ^ ννε, τΐί, ΜϊΓ-. «bga ·»

'χι:!' *. - r ■ s; ^_ ν ■ · ^[ ό : «rj.v'.l -r, ^ ¹ * .- I- ' ^: ~ ^r v> [- from l £ ö Ι ^ λ.ίοιι Vianet. *?

Λ 1 ί jCr '^'LU-'J';. ^! ö "'.' ί '''•".-! .. ■', o. ^{:: ■ '->'""ί 1} VO ^f lf-hVSÄ. ± <£." λΐΐ Iia ^r ^ ζ Igo: ¹

l -.r. f — ir / f / o -'η ι c- ^? ; s \ .vc: - r -., - v \ ^s . . (, r ν. · γ * ?; λΚ , au. · it! ar on · "

ΙΓ '. '! - "fs i .il ' v τ ,. ii. '. / θί · i'iivi ι · ζHi" \\: £ *. osl'cbo /.us gfv ^ spigment>/>: F -j' 3ü, v ν- ,. t

"Ό η,., Ι, ^_Γ " ·, ". .ι · ';.! . ". ⁱ ^: · ¹ : - \, - Γ-ίο ... ^ ··,; -,] ··. * ^ ivs l £ ^ Iy; -, _ρ ή ο- · L-- · \ er *>-.>·;'': ·· * »"')*' -: ^ -iLt '^ e ^ vc ^ e ^ r LcnFar ^ ίίί · η? 'c -J _5r J, -ς: - "-." ,, -_ Μ ... - ι, -'; 7 jr ^r · Vil: ^ ^ν "ί" ΐ

ϊ, -η »Λ - ...'- ⁱ M"'"« · η -,' -, ^ ^Λ 5 · - 'οι v / jir / n ϊ $; κ' · --ν

: VW>'V Τ "· Ζ' . <. Kjr - r - • τ; - '· I ^j -; r. _V ί'» ' ^Γ - ■ 1 -3, - «- : vr ° -; - '<^ r to? f € Γ Piv ^Γ OSii . »1 a-tj:" - ^ -or CU, .M "... \ <v :. ichuiv i'Mujr- ί, ni-h ^j i - ^ fJiijaa

£ ·?;, Τ.ΐ rj ' - «τ- ⁷ :.; Nr, 5 - ;. * .- · tr ο ν Γοε'-ri.j j, .- ..> ι Jc ü ^ jf ^; η 7 «- _f l ? t'j.oy Hls * · = "Tf \ .i (. {. \% ^{:, \ l ',} '! _< ^l ' ^j r; 7 · ^ ^Λ £ ί j. ^; , t'> 5 rix * ΐ ?; "^ 5 ', py.-Uil c ^., ^ οηηοΰβ

δθ ^r Z '«··· 5,1ο Eq? t'.oi-'i (.ί ri ^{, T} j : -v. "', · WJ 1 r \ .-. r; \ r _r , t VLfai- ni ^ Ou VoIuaHiteiUoft. v.tn-j ^ irrrota TN .-. Ι: Äs «: <ί '^ - υ :, t-, ■» wu ciii'-c ^ y ^ nan Ki ^s Iatal.II? Piv .1 at> 0 ~ - "- ^{, v} ">!; · '.: ··' \, t -'- l-. <■ ·> Jt- ¹ .: I '.of c'ivo- =

gfi?, e: it-sfcIetih siuVir · '>-'- ■ · -'. f ^! ':>' * ■ ^^ ..! I vÄi «ί, ·. ektioi. & ~

ßoüiiroh on 6i) -; 0 " ^! ^: · , - ..r'-j 3 · .... >'-Z-; tva .iu- * -» 5jUdv «» u kior -kbionr.-

t: η, C ei In 1,4 -t .λ -,? - C? ^{1 r} -λ · ■ 'l' c. >\>. * · ^: * Ir (j % VS '-'Vi, ι ens;'.: '·' V ...: , γ r., I "t - <·. * F " 1 "nil

fern a>, ".-i _ti L " i - '* ι'"", - ~ "\" I- ^{ ί \ i i '' - »$.%

l < λ ί * ι *> r -5 ·? \ - £, »/ <· '"r; «t i ' t ι» "' ¹ ' -, Λ ^r OI ι ·«. ι j- Su file ¹ Jiofiei ⁱⁱ ίΐ \ -ρ'ο ·. ^>. / ^ Ι. · * ' ^S t "15 *> ^{J <} -'''!' ^r VJ ^v &. »- <c ¹ ^: ¹ , Ti nt-, οι öS η,

Iii «ϊ»> .ΐλ ^ ο 3 "" ^, f? Lt. ^, 13 γ'ί ί ίώ * £ yV. i- ^ ⁱ '\ «" g aJ. cor A s Iz λ "xcn

ϊ, ίΐ fas i '>. "I ^j j. <- X ^t ' ί!,« ι ^ ρ. · 'c ^v ΰ Όϋ ^: ία , pr i, r, £ _c

Example 5

l ^ /. orsrlrf-to * i: -v. ^^ C '-. U'y' -! Ι ,; C _f ^l ^ ^f V - L ti Iv-LrcfjOjoacl rad Scr-ij.'Hc- ίώί Fi cf ', c , fx l ¹ ir, *!>'! ί γ »γ .ί ν · IJo ί Jii ρ ~ γ" Γ üams- *

^ fc ⁱ '-ι; ί £' sp: C Ki *, Ί ί "~> ί QV.,: l <]. '." ^r > l ^ .l Uf.i '"f' -. aSOGO

23 ^; i) L -ifei. j - «Mi = ..- '" il "', '^. >' ^ J'ikf ^ zT

ll'fil- unc ·>'-' ΐ l- ^r ) j 'o. Lv, iL 1 r LL; - ~; <\ -L "* ~ v ~ ^ cj _i S® i, Das

FtSSvk I ' ilO i-VrV' *. '! <... "''" L 'L ¹ 7' U ¹ ₁ 'i. 'L * ~ Γ "ti Os' ·

b. "ar,: a .5 '?! üti. τ \ Lv ¹ *'" v », ■ ν · α (,."("Jt" ^ i ». L« ';.

Llrv e; '' · 1 -C ... "v Pv / v '" ui Lv alkalis immediately üm

UßllLv vLuu (. Ir j, • -i ■ V.-. V ν-

Toi '^ j'i-j 6

- ^r : V Teilv '• ■ JJCi ^ iii -.ο:'''./^',- ViLCi- '·' - '-'ΰΐοώ Elf ⁱ SO Yoi _c « • I &ll'.o:., tr! ickn:, ru ^ i * ::, ·. ¹ Iu Vt r-; J.iSvLiL «κ tuv» vrhv- ^ nLsitO ^ Vis is a] lI ·· - Iresi 3 ^t J ⁵ Ojl ^, V- ^j Co Li-ri "ti 1 / 'o.13; --vj OorP ⁱ ii;? vic ν I trv j-rxLL EV £ JjJi, hi- ^\;; r.fiGtΐΓν, '% ·; -aoul .Gvj "iivLi.e?. ϊλϊ; ^γ ^ '.; 1 ·; Ϊλ "γπ1, ur ^ -

göbs'V Lit ■ ⁱ Zi, ' ' -ο o ^% '/ iflioAS, u j' ^ ivvv. ^ o "ί '> id Ir Qo --- LLoLcpb- Qtcrr ivii L: U, k \ <.: L \.; "-; - J : uvCfi ** i?: - Ä'ii / -i. \ S 0 * ^:; *: - · t> i . '. Oa & ^ aoJ' Atta (fi ⁱ ^ Gxy- ',? ^; · T ^ plt'iö: rl: vi, iao) '' i} C'i> ao ί ι ? .1ν s. Ctf ⁱ V · &' ⁱ L ^r I> .cvt VeirrUsn:

S _i ,? 'VlvJlr FPAPi:' V u V'oP «Lü 'ViT.", LvillC'V,. Ί ' • Iyr _l I ^r J ^ rn _p VWß. LUtSSÖÖ

7 -.:v_ ά '.ΐηι ir .tJ? t;: * ^; .Jc. · Λ. /. ' OO-Dfr ⁱ cvLi'Vi ,, η: iiVLH 'His,

Kcalctlc ^ -ν,:.; Ν ti j,; - ν, L ■ '. "Or;-; o ^ Liu ^ sv \ ä ν L-?. " » Rot' i ö © l R & aktions» gfyii & GliOO Sr * cä>c?;: fe ,. rj.-tcu; Uerzz: · * ILO " ³ Lesj-LLi (p« "w« t, ir 'fv, Df-.o on Ii Rsi t> '? Is \ ß> s? Ü. Μ υ KVgoYlio ^-i i ⁱ · 3t .c, iLLcA.4; k.LojL ■. · '.: ·; ·! / v?'" , rc'cc / 'l \ llkr®u Lr« es in: LVJ r - ^ r.uv ar- Ljo 'wiVi Lr:: s;, .- <;: Lc ^l -L /', L ν LtU'-i j.viov-

Iva? l "'-: r v c * -'-> Τ <· ^_.λ;;> - ■ -O <_''■ * ^- ν -J ¹ - · .ί' ^f T <*>Ο;

öe / ϊθ & S 'fcO-i ^ _: Tc .O'^; - OO O -j ·: - L · : ° '* V- "ν 0> ^: / U. Ί» ^ tvor ^ fvü; ~ Ot ι ur, T --j: l, O ^ ..lt. . I, -

¥?, 8ΰςρ Η- ·, ⁱ ^ ^t -L ^r r ϊ'ί. } - ,.: ζ.ΐΰ mi Ο. ι ·· »'θ", _v iO > * s L / -u ·

g ^ b- · = * roji ' ^j o: -: \ x- ' Λ -Ολ .: <; 0 <Ό das. uiuöslAöls © "blau, ® MsgengB" -y-fi, 7l-λ: .- " !: O OO / * ·> · ■ O

for example 7

6 v * .Uo rii-kcj iE.:-ifi u 'l' ^ '"^ Oi jjvv- biijiO Oi: >Vo" »« - T © slm> ί ^ ΓΚΟ'ο.-Ί O ^ OO "^ yOf. «L. < _f fl, o; ΟΟΟοϊμ-ϊι ^τ Ο. OOiO

Q2 ^ i of- IVxlc Ο.ί />. '. O OfOlOi · "SO ->■" Io-j _i .ii-.Oort -Λ uö-

f .; u ₅ - ^ .. c_f <· «i ⁵ i Oiit λή. \ jO roilti rOfcOOOOOi"0:> 7i * c: '»rOö vvfi 26 ^f £ ih < ν .-' · ι.: * -: ' Omi ^ OO * O -OO "- - • ■ ^^^

j)!.;,: ··>; ΌΟ, ..> τ: *>> i. rl · Orv -, ^ ju / .0 OO 0'.i>'au wu ⁱ Ο -' ^ θφ 3i.? ^ OO ^ ΟίΟΟϊΓ, ρ r ; KJj. ' --cv "; I / ViU 'L iOOn OO ' ." rii »f," lOt-i O _j -IioJ ¹ UV _r '

oj'i'i ¹ r 2 rl • .'Od oO,! i. «j->'" -Ό- .; OO',. ~;, 1? j, ..- r [.v 'j _la ?. »Tc '.' I Vec ^ :. ' kit .-- ^ Ο ": Ut- ,., iO i. ,> O. r ~ ^ Γ ., '· νι. j ^ rc ^. ^ clj ^ © -

SOG Ti, J ir, l '. \ ^{Ι Γί} »γ, -ί · '' tr PY L> ^ - j ^: λί ~" ^ς-α; Η.Γτ-: c _c ^'r; sti "\ S ^ -

ί / ΟΠ ',' ν, Ί,. ^t ^ f- '^ • S - * -? - ^ y ι. ' -,·1 -!: / 3Γζ \ ι?: ·; Τύ ', Ιϊ, ÜSI ί. '' '7th .-- 3 0Ζχ Ή -'3 ·) · '

Viii " rv- ' IF'"'. .-rc "'. -» a ·. -. ^t Vr-. "" «. ·'' ⁱ C. * - In / .χ Ao ??

F; oaa ± / 1 a -, <j: aA ϊΐιαα unit ii5 ycü ^ r IiFlAiA-ZhsA-IA vloosu ¹ anting-

ι ^ .λ - - a, Iv ;,. Haa aaaaa: · v / ÄtA3 Her ..? ' r, .j-, ... / ν '.,, ·;, .--.,. r »\ _«. ; ί · ei aj. '• / -J ..,; -> r, L <·'. f .-- y. ' ^s a A -.- *! χΙ., fs. ; o, vCJ ',. v: l Al: bio * a

1 - 'I *. i. : '·;'ι";." · -1 ·, ι Γj / v : -ό " 7 ".'"'l' ι- ΐ t · -'13 l ⁷ o3c" '£' si cn: 'u : am , r. ,, C ν> ~ o: -a. α.αϊ -,, n. - "Ir u.« / AIa * 1- a α \> a; / AuAÜa a "'/ l / ~"; a ι.''." A 'sv Γ "- AV' if / _; >.; ^ ₁ '... ·': _r . * · Λγλ *,« * ϊ;, «ν>« - 'j _i L "« Ί - "λ ^! Ί '' ^r · * I '. - ■ ca-a «, ua / 1 · ** / · * <■ ;? / a /"' ϊ ^f / ^, λ .ΐ ^, 3θ) ^, -ίΚ <Γ . ₍ ': οΙ Γ, υ /; _ ;,> / - !,'. ίΓ άα '! -' ··,: ο .. • a "i", '·. ⁱ JTo Γ >> / · AfAt / . ^ Ir • Cj>: ru ^ / aj Ia fc _e In til © ee & Ν. _T > v ', .. fA (ju'. '". Ι a r t. ' ·} ⁽ Ι • .O ^t 2 _n b .ι. i \ t AA- ⁱ ICAi ö.u ^ iiCA '.u ' C uia <3 ©? τ ν; .λΟ r γ ι "/"' : si- sc. =.}. ¹ A '· 3f. ^U j-: ό a / aa ~ ΙΟαΠ AÜTjtön

Κ ". J-.bi.Q" - "Aa 5'-, '·«, • Ar.- ,; Ci -Tf /,. ·. , ·; -;? ^ I>-; Γ \, -! κ ' tl-E: Η © Rk «

'ί C.'u.'y .-. ir.G'-fyi,. . '' t.! . ¹ O, w,, ^; .. ^: Α1 ν 1 S ₁ ^r SVZ ^ lV _s

qa ^ a t>: r '"Ati ^ j'hm' Tt- '' ■ I- 1.?.- a av./.Ά"<1,χ> iA * //, ι Ί-? ϋ Sai =

π ^ 1 <Αε 5, ί 'v. ": α · * ^{..> · α ί} α.α IIaYaA α- - vA _u 1 α" T "üAA <Ksl« - J ¹ I _i '. " j. r. ν t >>., '"A l ^f a ·.

'.Iolspicl 9

6 / γ: ' ¹ ' a, a- ,, j ° • i v.- ^ A: fA: ^ süA ^; A ;; orlan. ;; iit. ⁱ SO ¥ oL «

TcAXOL. -j;.? £ "AAC.jI: / A ·. ' v \ AAAAA; _f Ί'S: - '''■E.;) VAi hZulü ^ üOll KvlStBll «-

? aa «. Ί · Λ \ 53 , 1ί av.- A-> i:: -Ai / aaaa Ai ^fi 1Γ ίΑίΘ ^ ίΑΐ / ΐ ^ • ^ BGCisr »j ^? ?. ^; - " ^: ^ -i. ^r iO"' 1 _; a; 'a / av; - ·: '·' ·, - / ■ ■■ /> f '/ ^ λ ^ .ρ: · ' •. ⁱ I-AAA ^ lnn | ■ I— · -.- · - '-i · -. . . "-, '. · /.•.'.Zv " i • .I · ^; : - '. / ^! a - ', Lk

r: c ^T » 3 0-20 Pin, - '.'r gi ¥ o« dßß let,

.fi

ι.

V,?! - i J ", ^t . i V

V 'ΓΓ-' «=" "S

10 ⁱ Ik

V- "V>. '," .Υ ,''r f -5 ρ ϋ / ⁵ L Ji

... \: 3Γ.- rs: · . . • V. ^: · -. VtVxi ·; »ci wυ SOO ! Ropes

Ιί <Γ · ί · ^! .rV ι- · νν '' i '. 'U ' x JVjf _i OV r. ; rj W ι., τ θ uu V ⁱ 'fe: tl © n

5V i * * * .-; J t - ^ s ¹ '"« ^x O V> ■ - -. "Ν" . Iif / ii .; H vs.v.' ::. · V ¹ c. · Ϊ j V- c CV Vt cl "A &t",

ν fw. ν · ■; · ^J .rw ^; «-Λ _γ · - · -,. ί, 7 ^ ί ^ fz m & m *:

¹ ^ Sh , '.f -V' Γ. c ? = '■ · "·''• V tuWj>. ¹ V.! ·'./..'Wυ'-" ic .'V .. ton cV Τ '·? Χϊ V "

f. V. 'V' -v

ar : ⁱ ; ', c .; i'

V ',; /} ι ¹ - _{Vj 1} ; v ^r C · Vö ί'Λ. Fr ^ fo-

-: ', ί, - ^; \ wo «. '"-' · "ίίί '> vc <\ ν : < ' * * -i " * ■ <£. 'ν-? ^{1 r} j.'> 1/3 η Krsoy _p

ϊΛ: \ ^ _ί . '. λ ^, ί * "/ _> j:" - "• I ^1. ') ,, ';..; ε'.I·." λ., i-ν It λ; c , ^ .rn.euVMö «<

, -Xj , V : <> ·· - ·· y 5 ' lt », j Otc ^- S» "V *; \ -! •, -TE f: j"-G'itfeu Rof ₄ Ic ~ Ii - r .ii'Pi 'i ί r ^; r ° _t r ι .-- / · ",, f" f -.. "' C 'Λ;. · 1?,> iffv i .'. j * ,« in 1 ^r ZuJlprA

;., v; <^ "tt: i (.» 'IJ ^r ' .. i ' Cö: <; i <l "< 1' f l- LpL & ü 's" -vir Qftak'

.iC 't ' i '^' oi '/ l-'i .-. > \ "'stfe,"' v ~> L · Y ί .ι: "f ■ J- ^ ^ ^8. , '„ r:> t,

⁷ C '. "! C. ³ C ·.' Cl · · ', ' • '' t ¹ n "» ' Γ IV \! ~ Z <: ί. V Ί'Μ \ '' I _l Qi '4 I? J ί Vu Zo IfttZ> CU ^

Ψΐ, J. «-. legion Γ.;, - ;: rl νt,. ·· * ϊί .; ■ "» ">;, ä.» 11 '.-. Gjc Ϊλ lx ... ^ r) fvrii / ^ Mgögclien unci ίΛτχη u : 3 i & - » ^£, i ^ rc ' r 'w,"' ^ j ', ti, -i. "Fc < r ρ, · ::. 3 j I '. v. ^ c, 5 ^ '> - "' h! oP-"

;: Λ * 'Λΐί Αί . · ΛΖ ·:> ϊ. '.ί ^ ί ^Γ; - "· T ^K -tV'i > ^? R: · ';·; - ^ ..rr , .7 ?. !!' ■« '. ". Vtio ^^ Di; 3'JgC" -

λ ί -.ο -γ ^ Λ = e ^ g ^ lfc ν - -. ·.>" : \ lyd iic: .. av-i:;» _t i,. <v Ί? h: c: S / 'C-Td "' ö: r--"V'f-'- i ⁷ c "γ '/ i ⁱ r. . V ·: "ί '"^;"r. j ν, ν"> ν. ^ <Α: ν A -'-;'i.Iv>-iV'u: ^ r-

• j. ι. ⁱ C ⁱ i- ¹ i>. - i 5.Λ ·. ·> · '·. 7; 'Λ · ν> Ä ^f ■■ • I /, - fig-: \ ü «lck :; ; c "Ilii

; · P. η _; «, Ί ^; · _{T (} · ,, _t - '. ,, · - ■ {Ά ■ - "(L _t I' · '* ■ -.'·> ■ \ f .sV'jl ·. \ J \; 2li" V . "; ί'Ίΐί ^ V :.>> ■ I ^{'t T} \ _{λ ί} /": cI ^ SS "IIJ ^r Tii. ir; Q λ', 'υ / ι ι> \ *.!

^! ":" c '-f fr>ί' _v > - * 't: u iv ~; j ί * ulrü ^ a ^ ön.lot

/ «. < ¹ T t- ^: o .."t'K' ^} ■ ^; * - ⁵ ^ o «," ⁵ vciif /', ^: ^ν . "3 _Α ΰΣ?„ IJrL met Hmjißt & Mp & PE- = ΐ "c fb; jc) dU f.» ("■ / · '; _., ·. * .. Vr _i c ^s : It oh π-'Γ. · *> T. (LVi i ^ f" .t ™, V-' avs ⁱ IOC Ί ' θΙΙθο

i - '; f uOit ^' - jJ I ⁱ V- --I ^ir _i TiJPj ία '\ · „Τι ^ f,'',» · a " l: \\ (-.Oitjfc, / UiB

'V · ^ι · "',; J · '." ■ ''■>'- -ii · "- · '-'3'''.-V · Vw ί ^: · -ν v: su _: ^ ιΐοϊίΐά

: "or ^ o" f _ö c- - λ ";. * \ eVi'Ly- Ujk ί,: V'i;'f ^ υίΰ ί-fiO Τ'βί.Ιβη

'* ·'""'' - ι ^; "K ₁ " - V. L lit ES

'■;? <· Υ,. · * .. <: / - /; ·· f. · - ;. >, ~ · \. ',! J ä ^τ,; ί λ,. ^ij : t _f 'M-.r] . _f - _t r., r «t <jlei ^ 'ie? '' C · "i ¹ c ■.>'Γ-; t Λζ υ ⁱ i ^t i;'<.'«;,' re .. ■ '- S ^ Vύ ^; - · "' / If ^ ri _e

/ Tcxvr ·· Πί.'ν ..: * .. ν '"· - <· // - μ!.'. Vi- t'u.r ί <"? Ίϊν * ζ?, With 4 Yol _i -

j.'if ά ', ■■ Zi \ /.:- D ¹ Sw ^k :. -, / Iil · 5. ' ¹ J > r /. «; i ¹ _i ?; ^ » 5? -Iif riiV 'Pv Icii ₁ Jeo) ^

nid '-M Pv ^ cj''"-jrir.zt- Vi . ^T j ;' i nc: I If; Sl -Hi -Jsp Rsaktionsd ^ uoi · die Λ · -" · Li, -vi 1; • fj.'C'f.l " ^: j;?« ·>'''- Eq, .3 !'. C. ': .;> Ι -?':; ϊ , ι op ^ i-rontMc ^ Qi; in an -- > jr _; r Mu * 3 ι. "Ι- '"'>. 'A- \ 7 : - * ί Λ <"Π f; in'.>" *. I >. I,

, S = / "'/'~;, ¹ / k / '3. r .'li - ^' jn ... rr b i .a'jcf Zueata

ΉΓ ' , ^j J "<., .., />■,"·?'h:>/; L ί μ /. V ⁴ ν · Γ, / lc'ir * <* ^> _β ~

^! ji ¹ Lii / j '^ r " J /' T '^' in. " Lr /, »I>">. - 1 br / j .Vu <,> · ,. "Moid""^

C _ij G 'reite i ^ f ir-c- Xftf- ^ ^s -fjjTc ^ rayo (ücr-g.rf lollt nach

■; ϊΓ1 · Ι ·: '- ·>ν;' Im j r -.- i τ · ".ϊ>·' ^ · * - l / ^ rKtL · // ^ .uio- fasi

t '/ IX ./.-U'ar ; ^j ^ - ¹ '■ -. · "^'. ·· :.' .. · · · .Γ - '*' - ^ · ^ι:" iL \> -.? "Fv;'.- / tt ^r tr /; ^J vsi: ' gh at

f. C i

} J '. “Fr- w

ι '50,

T - r ·, j

if, '»αν?'

λ ^ Zi * j 2 g Iii

<? <"' - ^{i -Jc v} >*"' · * · ΐ'ι C ¹ Λ · -; -? '". {·; τ * Γ ,; ι <1 π- - Ab!", tVJh ^ r » Dsi *

- ⁵ S. ►.Yes OV ⁱ Tis -.br; ..j Λ "Ι \ .τ,.""=& r, <Yn ί>" · <^ κ: ~ j ■ J tv / '- sj <λγ terror ep

Claims (4)

I ₁ ,) Yei'f BhTQn ζην Ηθ3? Β to llung von Aoyliss ^s IAngeiaItteln _ii da « you? eh gakeanzelohnet, aase you QMmn ä @ 3? Formally JJ OQH HC ™ S0 "H. halide oä @ p ^ ovzugamlm treated with phosgene, 2.) Ve '« ' ..Μιί„ .ι ι Hss patent addressed I _i daSureh gakeasis © lehnet that chooses β ESfm Pyi ³ JfLr ρ Ir rartlBve Base. 3 ») Further training in Yerfataress according to Pateatanspsnxoii 2, characterized in that · the isan © rhattenen mixture noeh a stronger tertiary base ¹ ® ale Pyridln ^ as Triiaathylaiain or preferably Tyiäthylamln ^ on TTGT. 4.). Method according to Pstentaiisprueh 1, characterized in that Biaa Eis selects tertiary B-xo ^? ^. ^ H ^ Jsö r> - ve .sugBtraise Tri ätbylaaln uMär ^r . <"*« _ _S! See Sulfonsäur® chloric! Or phosgene »i 0 L- njnci, I ^» ~ c "u OPg ₀ LSsu Eigsmlttel performs "