DEF0010665MA - - Google Patents
Info
- Publication number
- DEF0010665MA DEF0010665MA DEF0010665MA DE F0010665M A DEF0010665M A DE F0010665MA DE F0010665M A DEF0010665M A DE F0010665MA
- Authority
- DE
- Germany
- Prior art keywords
- oxide
- cyclohexylidene
- rearrangement
- aniline
- reaction
- 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.)
- Active
Links
- -1 N-substituted carboxamides Chemical class 0.000 claims description 16
- 238000010438 heat treatment Methods 0.000 claims description 3
- 150000003857 carboxamides Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 230000008707 rearrangement Effects 0.000 description 8
- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 238000006462 rearrangement reaction Methods 0.000 description 5
- PPBBOELSIAPOOU-UHFFFAOYSA-N 1-phenylazepan-2-one Chemical compound O=C1CCCCCN1C1=CC=CC=C1 PPBBOELSIAPOOU-UHFFFAOYSA-N 0.000 description 3
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- QNWZMTWGSFHMRH-UHFFFAOYSA-N cyclohexyl(oxido)azanium Chemical compound [O-][NH2+]C1CCCCC1 QNWZMTWGSFHMRH-UHFFFAOYSA-N 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- HWFIBRXIRGWMDC-UHFFFAOYSA-N n-cyclohexyl-n-propylformamide Chemical compound CCCN(C=O)C1CCCCC1 HWFIBRXIRGWMDC-UHFFFAOYSA-N 0.000 description 2
- FNIKAGQFQKBVLX-UHFFFAOYSA-N n-cyclohexylbutan-1-imine oxide Chemical compound CCCC=[N+]([O-])C1CCCCC1 FNIKAGQFQKBVLX-UHFFFAOYSA-N 0.000 description 2
- MIUPVUSAABKKQX-UHFFFAOYSA-N n-cyclohexylbutanamide Chemical compound CCCC(=O)NC1CCCCC1 MIUPVUSAABKKQX-UHFFFAOYSA-N 0.000 description 2
- RPFGCUFAJAQNLJ-UHFFFAOYSA-N n-phenylcyclohexanimine Chemical compound C1CCCCC1=NC1=CC=CC=C1 RPFGCUFAJAQNLJ-UHFFFAOYSA-N 0.000 description 2
- 229940075930 picrate Drugs 0.000 description 2
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UEGMLNNXJSTTMM-UHFFFAOYSA-N 1-(4-chlorophenyl)azepan-2-one Chemical compound C1=CC(Cl)=CC=C1N1C(=O)CCCCC1 UEGMLNNXJSTTMM-UHFFFAOYSA-N 0.000 description 1
- PARABBHYKOZJTN-UHFFFAOYSA-N 1-(4-methylphenyl)azepan-2-one Chemical compound C1=CC(C)=CC=C1N1C(=O)CCCCC1 PARABBHYKOZJTN-UHFFFAOYSA-N 0.000 description 1
- URNBMJFMZCOROZ-UHFFFAOYSA-N CC=[N+]([O-])C1=CC=CC=C1 Chemical compound CC=[N+]([O-])C1=CC=CC=C1 URNBMJFMZCOROZ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000004508 fractional distillation Methods 0.000 description 1
- ORCIEIBZCKPMGC-UHFFFAOYSA-N hexyl(oxido)azanium Chemical compound CCCCCC[NH2+][O-] ORCIEIBZCKPMGC-UHFFFAOYSA-N 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 235000000396 iron Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ZEAUJQWDPKRESH-UHFFFAOYSA-N n,1-diphenylmethanimine oxide Chemical compound C=1C=CC=CC=1[N+]([O-])=CC1=CC=CC=C1 ZEAUJQWDPKRESH-UHFFFAOYSA-N 0.000 description 1
- IGWKEWGXGMHPRD-UHFFFAOYSA-N n-(2-methylpropyl)-1-phenylmethanimine oxide Chemical compound CC(C)C[N+]([O-])=CC1=CC=CC=C1 IGWKEWGXGMHPRD-UHFFFAOYSA-N 0.000 description 1
- SQFOKZCBFNORNB-UHFFFAOYSA-N n-(4-chlorophenyl)-1-phenylmethanimine oxide Chemical compound C=1C=C(Cl)C=CC=1[N+]([O-])=CC1=CC=CC=C1 SQFOKZCBFNORNB-UHFFFAOYSA-N 0.000 description 1
- CYKKBANDRNLJHN-UHFFFAOYSA-N n-(4-methylphenyl)cyclohexanimine Chemical compound C1=CC(C)=CC=C1N=C1CCCCC1 CYKKBANDRNLJHN-UHFFFAOYSA-N 0.000 description 1
- KSEWJQUSQWDBEE-UHFFFAOYSA-N n-(4-nitrophenyl)-1-phenylmethanimine oxide Chemical compound C1=CC([N+](=O)[O-])=CC=C1[N+]([O-])=CC1=CC=CC=C1 KSEWJQUSQWDBEE-UHFFFAOYSA-N 0.000 description 1
- UBINNYMQZVKNFF-UHFFFAOYSA-N n-benzyl-1-phenylmethanimine oxide Chemical compound C=1C=CC=CC=1C=[N+]([O-])CC1=CC=CC=C1 UBINNYMQZVKNFF-UHFFFAOYSA-N 0.000 description 1
- ZJLVWLICFJLAGC-UHFFFAOYSA-N n-cyclohexyl-1-phenylmethanimine oxide Chemical compound C1CCCCC1[N+]([O-])=CC1=CC=CC=C1 ZJLVWLICFJLAGC-UHFFFAOYSA-N 0.000 description 1
- QXDHNAZGAMSFHD-UHFFFAOYSA-N n-methylcyclohexanimine oxide Chemical compound C[N+]([O-])=C1CCCCC1 QXDHNAZGAMSFHD-UHFFFAOYSA-N 0.000 description 1
- RTRXYGSDWNVHBI-UHFFFAOYSA-N n-phenylcyclopentanimine Chemical compound C1CCCC1=NC1=CC=CC=C1 RTRXYGSDWNVHBI-UHFFFAOYSA-N 0.000 description 1
- MWBQWQYVNFFKFE-UHFFFAOYSA-N n-propan-2-ylpropan-2-imine oxide Chemical compound CC(C)[N+]([O-])=C(C)C MWBQWQYVNFFKFE-UHFFFAOYSA-N 0.000 description 1
- CDZOGLJOFWFVOZ-UHFFFAOYSA-N n-propylaniline Chemical compound CCCNC1=CC=CC=C1 CDZOGLJOFWFVOZ-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- VPCDQGACGWYTMC-UHFFFAOYSA-N nitrosyl chloride Chemical compound ClN=O VPCDQGACGWYTMC-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- XUWHAWMETYGRKB-UHFFFAOYSA-N piperidin-2-one Chemical compound O=C1CCCCN1 XUWHAWMETYGRKB-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Family
ID=
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