BE582745A - - Google Patents

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Publication number

BE582745A

BE582745A BE582745DA BE582745A BE 582745 A BE582745 A BE 582745A BE 582745D A BE582745D A BE 582745DA BE 582745 A BE582745 A BE 582745A

Authority

BE

Belgium

Prior art keywords

optionally substituted

acid

carried out

formula

tertiary amine

Prior art date

Links

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• 238000006243 chemical reaction Methods 0.000 claims description 18
• YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 12
• 238000000034 method Methods 0.000 claims description 12
• 239000002253 acid Substances 0.000 claims description 11
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
• 150000001412 amines Chemical class 0.000 claims description 10
• 150000003512 tertiary amines Chemical group 0.000 claims description 10
• 229910052757 nitrogen Inorganic materials 0.000 claims description 9
• 150000001875 compounds Chemical class 0.000 claims description 8
• -1 halogenated formic acid thioesters Chemical class 0.000 claims description 7
• 150000007970 thio esters Chemical class 0.000 claims description 7
• KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims description 6
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 6
• 125000005843 halogen group Chemical group 0.000 claims description 6
• 150000003839 salts Chemical class 0.000 claims description 6
• 230000015572 biosynthetic process Effects 0.000 claims description 5
• 229910052799 carbon Inorganic materials 0.000 claims description 5
• 125000001424 substituent group Chemical group 0.000 claims description 5
• 238000003786 synthesis reaction Methods 0.000 claims description 5
• 230000001131 transforming effect Effects 0.000 claims description 5
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 4
• 150000001298 alcohols Chemical class 0.000 claims description 4
• 125000003277 amino group Chemical group 0.000 claims description 4
• 150000001721 carbon Chemical group 0.000 claims description 4
• 125000000623 heterocyclic group Chemical group 0.000 claims description 4
• GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 claims description 3
• 150000002148 esters Chemical class 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 238000004519 manufacturing process Methods 0.000 claims description 3
• 150000002825 nitriles Chemical class 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical class NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
• IJCVBMSXIPFVLH-UHFFFAOYSA-N [C].S=O Chemical compound [C].S=O IJCVBMSXIPFVLH-UHFFFAOYSA-N 0.000 claims description 2
• 125000000217 alkyl group Chemical group 0.000 claims description 2
• 125000002947 alkylene group Chemical group 0.000 claims description 2
• 150000002780 morpholines Chemical class 0.000 claims description 2
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
• 150000003457 sulfones Chemical class 0.000 claims description 2
• 150000003242 quaternary ammonium salts Chemical class 0.000 claims 2
• MJGPTHPXMVMHPS-UHFFFAOYSA-N 1,3,2-dioxathietan-4-one Chemical class O=C1OSO1 MJGPTHPXMVMHPS-UHFFFAOYSA-N 0.000 claims 1
• 125000004432 carbon atom Chemical group C* 0.000 claims 1
• 239000002184 metal Substances 0.000 claims 1
• 125000004193 piperazinyl group Chemical group 0.000 claims 1
• KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 claims 1
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 60
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
• 239000000155 melt Substances 0.000 description 14
• 239000002904 solvent Substances 0.000 description 10
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 9
• 239000000203 mixture Substances 0.000 description 9
• 239000008096 xylene Substances 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
• 239000000047 product Substances 0.000 description 6
• 238000004821 distillation Methods 0.000 description 5
• GABQKHQNXWNJJJ-UHFFFAOYSA-N diphenylcarbamic acid Chemical compound C=1C=CC=CC=1N(C(=O)O)C1=CC=CC=C1 GABQKHQNXWNJJJ-UHFFFAOYSA-N 0.000 description 4
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• XNBKKRFABABBPM-UHFFFAOYSA-N n,n-diphenylcarbamoyl chloride Chemical compound C=1C=CC=CC=1N(C(=O)Cl)C1=CC=CC=C1 XNBKKRFABABBPM-UHFFFAOYSA-N 0.000 description 3
• OHHIBZKYXJDQEU-UHFFFAOYSA-N 3-chloro-n-phenylaniline Chemical compound ClC1=CC=CC(NC=2C=CC=CC=2)=C1 OHHIBZKYXJDQEU-UHFFFAOYSA-N 0.000 description 2
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
• 238000009835 boiling Methods 0.000 description 2
• DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 2
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
• 238000001953 recrystallisation Methods 0.000 description 2
• 238000010992 reflux Methods 0.000 description 2
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
• VMSLCPKYRPDHLN-UHFFFAOYSA-N (R)-Humulone Chemical compound CC(C)CC(=O)C1=C(O)C(CC=C(C)C)=C(O)C(O)(CC=C(C)C)C1=O VMSLCPKYRPDHLN-UHFFFAOYSA-N 0.000 description 1
• MKASXAGBWHIGCF-UHFFFAOYSA-N 3-methoxy-n-phenylaniline Chemical compound COC1=CC=CC(NC=2C=CC=CC=2)=C1 MKASXAGBWHIGCF-UHFFFAOYSA-N 0.000 description 1
• SEKMXHXGKOKENQ-UHFFFAOYSA-N 4-ethoxy-n-phenylaniline Chemical compound C1=CC(OCC)=CC=C1NC1=CC=CC=C1 SEKMXHXGKOKENQ-UHFFFAOYSA-N 0.000 description 1
• OBHGSIGHEBGGFS-UHFFFAOYSA-N 4-methoxy-n-phenylaniline Chemical compound C1=CC(OC)=CC=C1NC1=CC=CC=C1 OBHGSIGHEBGGFS-UHFFFAOYSA-N 0.000 description 1
• AGHYMXKKEXDUTA-UHFFFAOYSA-N 4-methyl-n-phenylaniline Chemical compound C1=CC(C)=CC=C1NC1=CC=CC=C1 AGHYMXKKEXDUTA-UHFFFAOYSA-N 0.000 description 1
• JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
• MZVQCMJNVPIDEA-UHFFFAOYSA-N [CH2]CN(CC)CC Chemical group [CH2]CN(CC)CC MZVQCMJNVPIDEA-UHFFFAOYSA-N 0.000 description 1
• 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
• 125000004429 atom Chemical group 0.000 description 1
• 150000001805 chlorine compounds Chemical class 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 125000000753 cycloalkyl group Chemical group 0.000 description 1
• 229960003750 ethyl chloride Drugs 0.000 description 1
• 238000001704 evaporation Methods 0.000 description 1
• 230000008020 evaporation Effects 0.000 description 1
• 239000000706 filtrate Substances 0.000 description 1
• 238000000227 grinding Methods 0.000 description 1
• 238000002844 melting Methods 0.000 description 1
• 230000008018 melting Effects 0.000 description 1
• 150000002736 metal compounds Chemical class 0.000 description 1
• HUDSSSKDWYXKGP-UHFFFAOYSA-N n-phenylpyridin-2-amine Chemical compound C=1C=CC=NC=1NC1=CC=CC=C1 HUDSSSKDWYXKGP-UHFFFAOYSA-N 0.000 description 1
• XTEGVFVZDVNBPF-UHFFFAOYSA-L naphthalene-1,5-disulfonate(2-) Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1S([O-])(=O)=O XTEGVFVZDVNBPF-UHFFFAOYSA-L 0.000 description 1
• 125000002560 nitrile group Chemical group 0.000 description 1
• 239000003208 petroleum Substances 0.000 description 1
• 150000004885 piperazines Chemical class 0.000 description 1
• 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
• 239000007787 solid Substances 0.000 description 1
• 230000002048 spasmolytic effect Effects 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 238000003419 tautomerization reaction Methods 0.000 description 1
• 150000004886 thiomorpholines Chemical class 0.000 description 1
• 125000005853 β-dimethylaminoethyl group Chemical group 0.000 description 1