DD263192A3 - Verfahren zur darstellung von n-arylderivaten des n',n'-dimethylharnstoffes - Google Patents
Verfahren zur darstellung von n-arylderivaten des n',n'-dimethylharnstoffes Download PDFInfo
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- DD263192A3 DD263192A3 DD85277222A DD27722285A DD263192A3 DD 263192 A3 DD263192 A3 DD 263192A3 DD 85277222 A DD85277222 A DD 85277222A DD 27722285 A DD27722285 A DD 27722285A DD 263192 A3 DD263192 A3 DD 263192A3
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- German Democratic Republic
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- mojih
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- yrjiepofla
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Abstract
Das Verfahren zur Darstellung von N-Arylderivaten des N,N-Dimethylharnstoffs der allgemeinen Formel (1), Wobei R1, R4 und R5H, CH3, C2H5, R2H, Cl, CF3, R3H, Cl, OCH3, CH3 sind, besteht in der Reaktion von Dimethylamin mit Kohlenoxidsulfid bei einem Molverhaeltnis von 2,75...4:1 und 5...20C in Tetrachlorethylen unter nachfolgender Behandlung des Reaktionsprodukts mit einem Anilinderivat der allgemeinen Formel (2), wobei R1 bis R5 die o. g. Bedeutungen haben. Formel (1) und (2)
Description
OIMCAHHS H30EPETEHHH K ABTOPCKOW 3aHBJieHo: 15.02.83 3aHBKa: » 3552426/23-04 MkA C 07 C 127/19; C 07 C 127/15 Abtoph: T.M.lHaMcyTjCHHOB, 3.M.IIojiy3KTOBa, P.B.BajniTOB,
C.H.Ckjihp, B.JUChmohob, A.B.CTapKOB 3affBHTejrb: π/η Β-877Ι
H300peTeHHtf: CnOCOB IIOJEHSHHfl N-APHJIIIP0M3-
BOJlHBiX N»,N * -JJ^THJIMO1ISBHHbI
Η3θόρβτβΗΗθ OTHOCHTCH κ ycoBepiueHcTBOBaHHOMy cnoco-
odmeä φ
NHCON(CH3)2
(I)
R3=HjCIjOCH3,CH3
φopMyJIH (I) ΠρΗΜβΗΗΙΟΤΟΗ B CeJT&CKOM XO-
3HHCTBe KaK repdiEJCHjiH jsjiK dopBdn c copHHKaMH. H3BecTeH cnocod nojiy^eHHH coe;njiHeHHH
( R1 ^ R2 = R5 = H, R3 = OCH3, R4 = Cl Br B3aHM0,H;eHCTBHeM SKBHMOJIHpHHX KOJDFieCTB H 3-XJIOp-(HJIH 3 - 6ρθΜ)-4-ΜβΤΟΚΟΗφθΗΐυΐΗ3QIJHaHaTOB B boähom pacTBope npn 5-1O0C ( CH , A, 466943). Cnocod odecne^HBaeT βηοοκηθ bhxoäh n;ejieBHX npo^yKTOB (90-95$).
η TpyjmojiocTynHHx H3on.HaHaTOB, β npoiiecce CHHTe3a κο-TOPHX HCnOJH,3yeTCiI BHCOKOTOKCHHHHH φΟΟΓΘΗ.
HaHdojiee djni3KHM κ HacTonmeMy no Texmi^ecKof cym-HOCTH η jiocTHraeMOMy pe3yjn>TaTy ηβ,πηθτοη cnocod nojiy-
φopMyJIH I B3aHMo;o;eHCTBHeM cepooKHCH
- 2 yrJiepoßa c ßHMeTHJiaMMHOM β TOJiyone πρπ οοοτηοιπθηηη Haa-
peareHTOB 1:1:7 η KOMHaTHoii TeMnepaType c nocjiejsjs oöpaöoTKOii θκβηποληρηημ no οτηοιπθηηιο κ cepooKHCM yr-
KOJiHtiecTBOM cooTBeTCTByiomero aaMemeHHoro npn TeMnepaType 80-980C ( us , A, 2655534). β (2) 3KcnepMMeHTajibHbiM npwMep npoiiecca c ytiacTMeM β Ka-3aMemeHHoro aHMJiHHa, η - xjiopaHHJiHHa noKa3H-
ντο coeflMHeHHe I ( R1=R3=R^=R5=H, R^=Cl )no
c βηχο,π,ομ 72,5%. Cnocoö xapaKTepn3yeTCfl hhskhm
Η3θ6ρβτβΗΜΗ HBJineTca noBbimeHHe BbixoAa ro npoflyKTa.
nocTaBJieHHaa qejib AocTHraeTCH cnocoöoM
N-apHJinp0H3B0AHbIX N f , W' -flHMeTHJIMO^eBHHbI
<$opMyjibi I, rfle R^R45R5 = H,GH3,C3H5; R2 = H,Gl,CF3; R^ = H,oi,ocH^,CH^,nyTeM B3anM0fleiicTBna flHMeTHJiaMMHa c cepooKHCbK) yrjiepofla β cpe,ne TeTpaxjiopaTHJieHa πρκ τθμπθ paType 5-2O0C μ MOJibHOM οοοτηοπιθημη AHMeTMaMHHa η cepooKHCH yrjiepofla 2,75 - 4:1 c nocjieflyioiijeii oöpaöoTKoM
BHineyKa3aHHbie 3HatieHHH, πρΗ nepaType 90-920C.
B3aHM0#eMCTBHH ,D1HMeTMJIaMHHa C CepOOKHCbIO
5-200C, MOJibHoe cooTHomeHHe ßHMeTHJiaMHHa κ cepooKHCH yrjiepofla 2,75-4:1, Hcnojib3OBaHHe β KaxiecTBe opraHHqecKoro pacTBopHTejin TeTpaxjiop3THJieHa.
Mcn0JIb30BaHHe H3ÖbITKa flHMeTHJiaMHHa ΠΟ OTHOmeHHK) K
cepooKHCH yrjiepofla CBHine 4:1 Heu;ejiecoo6pa3HO, TaK κ HeonpaBflaHHO öojibiiiOMy pacxofly aMHHa.
.0 if; Q]- -'.'.; 392 /
peaKDHM πρπ TeMnepaTypax ΗΗκβ 50C HeueJiecoo6pa3 HO, TaK KaK. πρΜΒΟβΗΤ κ ycJiOKHeHHK) τθχηολογμη npouecca b CBH3H c HeoÖxoflHMOCTbfo noAAepjKaHHH hk3koh TeMnepaTypH. Μ3θ6ρβτβΗΗβ HjiJiiocTpMpyeTca npwMepaMH I-14. CpaBHHTejibHHM πρΗΜβρ 15 noKa3HBaeT Heqejiecooöpa3-
HOCTb ΠρΜΒβΑβΗΜΗ npoqecca npH COOTHOJiieHHM AMMeTHJIaMMHa K cepooKMCH yrjiepofla μθηθθ 2,7-1. CpaBHHTejibHHii npHMep 16 noKa3bmaeT HeiiejiecooöpasHocTb προεβ^βΗΜΗ npoi^ecca npw TeMnepaTypax BHine 2O0C.
ΠρΜΜβρ I. ·
B KOJißy, coflepÄamyio 100 mji TeTpaxjiopaTHJieHa, πρκ nepaType I0-I5°C nponycKaioT β TetieHHe 1,5 yaca. 8,4 r' (0,14 MOJiH) cepooKMCM yrjiepofla η 25,4 (0,56 MOJieö) TMJiaMMHa, MOJibHoe cooTHOüieHne 1:4. 3aTeM floöaBJiaKjT 20 r
(0,127 MOJIH) Π ( R1=R4=R5=H, Rg=Cl, R3=OGH3)
noflHHMajoT TeMnepaTypy flp 920C n BfcmepscHBaioT β TetieHne 12 ^iaCOB. ΟΤΓΟΗΗΙΟΤ M3ÖbIT0K ,D1HMeTPIJIaMHHa, pa36aBJIHK)T OC-TaTOK ropH^en BOfloü, oxJiajiCAaioT ρ,ο KOMHaTHoM TeMnepaTypbi, BbinaBIUHii OCaftOK OT(|>HJIbTpOBbIBaiOT, npOMHBaiOT XOJIOäHOH BOflOii η cymaT. IIojiyxiaioT 28,5 r ( R1=R4=R5=H, R2=Cl, R3=OCH3 ) TeMnepaTypa njiäBJieHHH 126-1270C. Bbixoä 98,2/ζ, ocHOBHoro BemecTBa 99,85SS.)
IIpHMep 2.' "
ripoiiecc BeflyT KaK β npHMepe I, ho KOJiHuecTBO
cocTaBJineT 18,86 r (0,42 mojih), cooTHOineHHe ah η cepooKHCH yrjiepo.ua 3:1. IlojiyTiaioT 28,3 r
( R1=R4=R5=H, ' R2=Cl, R3=OCH3 ).BHXOA 97,5%.
ΠρΗΜβρ 3.
IIpoiiecc BeAyT KaK β npHMepe I, ho KOJiM^iecTBo cepo-OKHCH yrjiepoAa cocTaBJineT 13,44 r (0,2 2 mojih), 40,32 r (0,89 MOJien), β Ka^ecTBe HcnojibsyioT Π ( R1=R4=R5=H, R2=R3=Cl ) β
33 r (0,2 mojih). IIojiyxiaioT 46,5 r (97,9%) I ( R1=R4=R5=H, R2=R3=Ci ), TeMnepaTypa 158- 9 C, coAepacaH«e οοηοβηογο Beii^ecTBa 99,5%.
-S. IP. 37
2 t> Δ I
- 4 ΠρκΜβρ 4
riponecc Beflyr Kan β npHMepe I, ho KOJinqecTBO cepo-
yrjiepo^a cocTaBJineT 15,53 r (%625 MOJiefi) MHHa 34,9 r (0,77 MOJieii), MOJibHoe οοοτηοπιθηηθ Ha κ cepooKHCH yrjiepo^a 3,1:1. B KatiecTBe npon3BO,n,Horo
Hcrtojib3yioT Π ( R.J=R3=R4=R5=H , R3=Cl ) β
30 r (0,23 mojih). IIojiytiafOT 45,8 r (98,2%) I ( R1=R2=Ry1=Rc-=H , Ro=Cl ). TeMnepaTypa nJiaBJieHHH
174- 5 C, co^epscaHwe ochobhopo BemecTBa 99,6%. ΠρΗΜβρ 5.
B KOJiÖy no 100 mji TeTpaxJiopaTHJieHa πρπ TeMnepaType I0-I5°C nponycKaroT 14,19 r (0,22 mojih) cepooKHCH yrjiepo-η 31,9 r (0,7 mojih) AMMeTHJiaMHHa, cooTHOuieHHe flHMeTHJia-κ cepooKHCH yrjiepoßa 3,2:1. 3aTeM ßodaBJiaiOT 20 r
(0,2 MOJIH) np0H3B0AH0r0 aHHJIHHa Π ( R1 - R5 = H )♦ TeM-
nepaTypy no^HHMajOT flo 9O0C, cMecb nepeMeoiHBaioT β TetieHHe 2 qacoB, oöpaßaTHBaroT KaK β npwMepe I. .FIojiyqaioT 34,2 r (97%) I ( R1 - R5 = H ) TeMnepaTypa njiaBJie-
HHH 135- 60C, coflepacaHHe οοηοβηογο Be^ecTBa 99,7%. IlpHMep 6.
Ilpoijecc Be^yT KaK β npHMepe I, ho TeMnepaTypa nepBOii CTaflHH cocTaBJineT 150C, KOJinxiecTBO cepooKHCH yrjiepofla (15,53) (0,25)mojih), ^MeTHJiaMHHa 39,7 r (0,875 mojih) cojopiMeTHJiaMHHa κ cepooKHCH yrJiepofla 3,5:1, β KanpoH3BOAHoro aHHJiHHa Hcnojib3yioT 36,7 r 0,228 MOJien) Π ( R1=R3=R4=R5=H , R2=GP3 ). riojiyqaioT 52,04 r (98,4%) I ( R1=R3=R4=R5=H , R2=GP3 ), TeMnepaTypa ruiaBJieHHH 163- 4 C, coßepscaHHe οοηοβηογο BenjecTBa 99,3%, IIpHMep 7.
npouecc BeflyT β npHMepe I, ho TeMnepaTypa nepBOii cTa-1O0C, KOJiHtiecTBO cepooKHCH yrjiepofla 12,3 r (0,2 mojih), 27 r (0,6 mojih), a β Ka^ecTBe npoH3BOflHoro
aHHJIHHa HCnOJIb3yK)T Π ( R1=R4=R5=H, R2=CIjR3=CEp B KOJIH-
qecTBe 25,47 r (0,18 mojih). uojiynaioT 37,52 r (98,1%) I (R1=R4=Rc=H, R2=Cl, R3=CH3 ), TeMnepaTypa 147- 8 C, coßepjKaHHe οοηοβηογο BenjecTBa 98,
π ·λ7
ΠρΕΜβρ 8. · nporiecc BesyTjKaK β npuMep'e I, ho TeMnepaTypa nep-
boh CTaAHH 2O0C, KOJii'FiecTBO cepooKiicH yrjieposa 13,2 r (0,22 MOJiH) ÄHMeTHJiaMHHa 27 r (0,6 mojih), cooTHOiiiemie OTMeTHJIaMHHa κ cepooKHcs 2,75:1, β Ka^ecTBe npOH3BOÄHoro aHHJIHHa HCnOJIESpJT Π ( R1= Rc= C2H5, R2-^a = H) B KOJIH-
30 r (0,2 mojlh). üojiyqaioT 43,34 r (98,5$) I ( R1 = CpHg, Rp""R4 = H) * TeMnepaTypa njiasjieHHH 184- 5 C1
οοηοβηογο BeiiiecTBa 99,4$. IIpHMep 9.
Ilpoiiecc Bejiji, KaK β npmviepax 1,6, ho KOjnraecTBo cepooKHCH yrjiepofla 13,2 r (0,22 mojih), £KMeTHJiaMHHa 31,5 r-(0,7·mojih), cooTHOineHne ,HHMeTHjiaMHHa κ cepoOKHCH yrjieposa 3,2:1, β Ka^ecTBe npoH3BOÄHoro anmmHa HcnojiL3yiOT Π( R1= =CHg, R5= ^2^5* R2~R4 = H) β KOjrH^ieCTBe 27,2 r (0,2 mojih ).. riojiy^iaiOT 4O.,5 r (98,4^)I( R1= CH3, R5= C2H5, '? R2-R. = H), TeMnepaTypa njiaBJieHHH 147- 8 C1 co^epscaHHe οοηοβηογο BeuteCTBa 99,4$
10.
KaK β npHMepax 1,9, ho TeMnepaTypa
nepBot cTaÄiiH 100C, B KanecTBe προη3βοαηογο aHHjmHa hcnojiB3yiOT 24,4 r (0,2 mojih)II( R1= R3 = CH3, R2= R4= Rg =
1 3 3 2 4
= H). nojiyqaioT 37/78 (98,4$) I ( R1= R3= CH3, R2= R4 = = R5 = H), TeMnepaTypa njiaBJieHHH 135- 60C, co#ep}KaHHe οοηοβηογο BemecTBa 99,5^.
ΠρπτΛθρ II.
npoiiecc Be^yT, KaK β npro/iepax 1,9, ho TeMnepaTypa
nepBoI CTaAHH 2O0C β Ka^iecTBe npoH3Bo;D;Horo amuniHa hcnojiL3yiOT 24,4 r (0,2 mojih) Π (R1= R = CH3, R2= R3= R5= = H). nojiyqaioT 37,8 r (98,5^) I ( R1= R4='CH3, R2= R3= = R5= H), TeMnepaTypa iuiaBjienHfi 138- 90C, co^epjKaHHe οοηοβηογο BeiiiecTBa 99,3^.
IIpHMep 12.
npoiiecc Be.nyT, KaK β npHMepax 1,9, ho TeMnepaTypa nepBoS cTaiCHH 150C, β KanecTBe npoH3BPflHoro aHHjniHa hc-
nojiL3yiOT 20,8 r (0,2 mojih) Π ( R2= CHg, R1= R ' = R. = = R5 = H). nojiy^aiOT r (98,4%) I ( R2= GHo, R1= R3=
= R. = R5 = H), TeMnepaTypa njiaEJieHHß 144- 5 C, coßepHca
HHe OCHOBHOrO BeIIJeCTBa 99,4$. - -·
npnMep 13. '
npoiiecc BeAyT, KaK β npmwepe I, ho TeMnepaTypa nep-BOM cTaflnn (B3anM0ii;eicTBHH cepooKHGH yrjiepofla c MHHOM) 50C. BhXOä I (R1= R4 = R5 = H, R2=Cl , R3 =
= OCHo), 98,1%,. CO^epfanne οοηοβηογο BeinecTBa 99,8^. ΠρΗΜβρ 14. . .
npoiiecc BeayT, KaK β npmiepe I, ho TeMnepaTypa nep-
BOH CTaJiEH 2O0C. BtKOA I ( R1= R. = R5 = H, . R2= Cl ,
OCH), 98,04%, coflepacaHne οοηοβηογο BemecTBa 98,8%
:I5 (cpaBHHTejIBHHfl). -
Ilpoixecc Be,nyT, KaK BnpHMepe I, ho KOjnraecTBO
12,5 r (0,27 mojih), οοοτηοπιθηηθ ÄHMeTHJiaMHHa h cepooKHCH yrjiepoflia 1,9:1, Bhxoä I ( R1= R. = R5 = H, R2 = Cl , R3= OCHg), 88,9%, TeMnepaTypa njiaBJieHHH 121- - 40C-, coßepjKaHHe οοηοβηογο BemecTBa 92,7%.
CpaBHeHHe pe3yjiBTaT0B c nojiy^eHHHMH β npHMepe I no-Ka3HBaeT, ^το yMenmieHHe οοοτηοιπθηεη iiHMeTHJiaMHHa η cepooKHCE yrjiepoÄa BH3HBaeT naÄeHHe. BHXoiia η-ώιοτοτη iiejie-ΒΟΓΟ npOjDQTKTa.
IIpHMep 16 (cpaBHHTeJIBHHH).
IIpoiiecc BeiiyT, KaKB npHMepe'4, ho TeMnepaTypa nep-BOil CTaAHH 250C. Blixoä I ( R1= R2 = R. = R5= H, R3= Cl ) 90,0%, coflepEaHPie οοηοβηογο BeinecTBa 90,8%.
CpaBHeHHe pe3yjiBTaT0B c nojiyqeHHHMH β npHMepe 4 no-Ka3HBaeT, hto yBejuraeHHe TeMnepaTypn B3aHMo;n;eicTBHfl mc cepooKHCBio yrjiepoßa πρηβοαητ κ noKimemno bh-
η "ήίοτοτη iiejieBoro npojr/KTa.
ΠρπΜβρΗ I-14 noKa3BiEaIOT, ^TO cnocoö noj^^eHHfl coeflH-
HeHHH I B COOTBeTCTBEH C Η300ρβΤΘΗΗΘΜ nO3BOJIHeT POBHCHTB iiejieBHx προίτ/κτοΒ ε .oöecne^HEaeT hx BticoKyio
-^r- n ^ —
Claims (1)
- Μ30ΒΡΕΊΈΗΗΗClIOCOO nOJiy^eHEH N-apHJHipOHSBOßHHX Ν',Ν'-,oömeM cJopMyjiHi · ·NHCOIi(CH3) 2(I): R1, R4, R5 =H,CH3, G2H5; R2= H,Cl,CP3 ; R~ = H, Cl,OCHo,CHo BsanMDfleäcTBHeM ÄHMeTHJiaMHHa c cepooiiHCLio yrjiepofla β opraHZ^ecKOiM pacTBopnTejie c nocjie-Η OÖpaÖOTKOH ΠΡ0Η3Β0ΑΗΗΜ 3HHJIHHaKH2.1^ BHineyKa3aHHHe 3Ha^eHHH, npH TeMnepa-Type 90-92 C, OTiz^aimiilcH τβΜ, C IiejIBE) ΠΟΒΗΠΙΘΗΖΗ BHXO^a ΙίθΛβΒΟΓΟBHe ÄEMeTHjraMHHa cepooKHCBio yrjiepo^a προεο^Ητ πρρΐ τθμπθ-paType 5-2O0C η mojibhom cooTHomeHHH ÄHMeTHJiaMHHa π cepoyrjiepofla .2,75 - 4:1, a β Ka^ecTBe opramraecKoro ncnojiB3yioT
Priority Applications (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DD85277222A DD263192A3 (de) | 1983-02-15 | 1985-06-10 | Verfahren zur darstellung von n-arylderivaten des n',n'-dimethylharnstoffes |
CS854168A CS266472B1 (en) | 1983-02-15 | 1985-06-11 | Preparation method of n-arylderivatives n',n'-dimethylurea |
BG70645A BG46960A1 (en) | 1983-02-15 | 1985-06-12 | Methodf or preparing of n-aryl derivatives of n, n- dimethyl carbamide |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SU3552426/04A SU1119310A1 (ru) | 1983-02-15 | 1983-02-15 | Способ получения n-арилпроизводных- n′, n′ -диметилмочевины |
DD85277222A DD263192A3 (de) | 1983-02-15 | 1985-06-10 | Verfahren zur darstellung von n-arylderivaten des n',n'-dimethylharnstoffes |
CS854168A CS266472B1 (en) | 1983-02-15 | 1985-06-11 | Preparation method of n-arylderivatives n',n'-dimethylurea |
Publications (1)
Publication Number | Publication Date |
---|---|
DD263192A3 true DD263192A3 (de) | 1988-12-28 |
Family
ID=27179450
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DD85277222A DD263192A3 (de) | 1983-02-15 | 1985-06-10 | Verfahren zur darstellung von n-arylderivaten des n',n'-dimethylharnstoffes |
Country Status (3)
Country | Link |
---|---|
BG (1) | BG46960A1 (de) |
CS (1) | CS266472B1 (de) |
DD (1) | DD263192A3 (de) |
-
1985
- 1985-06-10 DD DD85277222A patent/DD263192A3/de unknown
- 1985-06-11 CS CS854168A patent/CS266472B1/cs unknown
- 1985-06-12 BG BG70645A patent/BG46960A1/xx unknown
Also Published As
Publication number | Publication date |
---|---|
CS416885A1 (en) | 1988-02-15 |
BG46960A1 (en) | 1990-04-16 |
CS266472B1 (en) | 1990-01-12 |
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