NO135143B - - Google Patents

Info

Publication number

NO135143B

NO135143B NO160572A NO160572A NO135143B NO 135143 B NO135143 B NO 135143B NO 160572 A NO160572 A NO 160572A NO 160572 A NO160572 A NO 160572A NO 135143 B NO135143 B NO 135143B

Authority

NO

Norway

Prior art keywords

formula

hydrogen atom

methyl

compound

group

Prior art date

1972-05-05

Links

• Espacenet
• Global Dossier
• Discuss

• 150000001875 compounds Chemical class 0.000 claims description 23
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 9
• 238000002360 preparation method Methods 0.000 claims description 9
• 150000003839 salts Chemical class 0.000 claims description 9
• 238000006243 chemical reaction Methods 0.000 claims description 7
• 238000000034 method Methods 0.000 claims description 7
• 125000000217 alkyl group Chemical group 0.000 claims description 6
• 125000001424 substituent group Chemical group 0.000 claims description 6
• 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
• 125000002252 acyl group Chemical group 0.000 claims description 5
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
• -1 1,2-diphenylethyl group Chemical group 0.000 claims description 4
• 238000005985 Hofmann elimination reaction Methods 0.000 claims description 3
• 239000002253 acid Substances 0.000 claims description 3
• 239000003513 alkali Substances 0.000 claims description 3
• 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 3
• 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
• 150000001450 anions Chemical class 0.000 claims description 2
• 150000007522 mineralic acids Chemical class 0.000 claims description 2
• 125000004998 naphthylethyl group Chemical group C1(=CC=CC2=CC=CC=C12)CC* 0.000 claims description 2
• 150000007524 organic acids Chemical class 0.000 claims description 2
• 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
• 125000005843 halogen group Chemical group 0.000 claims 1
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
• 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
• 229910052739 hydrogen Inorganic materials 0.000 description 8
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
• 239000001257 hydrogen Substances 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
• QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 4
• 239000011541 reaction mixture Substances 0.000 description 4
• 238000010992 reflux Methods 0.000 description 4
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
• 238000004519 manufacturing process Methods 0.000 description 3
• 238000001953 recrystallisation Methods 0.000 description 3
• 229910052938 sodium sulfate Inorganic materials 0.000 description 3
• 235000011152 sodium sulphate Nutrition 0.000 description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
• NSLKFRGZLUIUKO-QWRGUYRKSA-N 6,7-benzomorphan Chemical compound C1C2=CC=CC=C2[C@H]2CCN[C@@H]1C2 NSLKFRGZLUIUKO-QWRGUYRKSA-N 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
• TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 2
• 229910021529 ammonia Inorganic materials 0.000 description 2
• 239000002585 base Substances 0.000 description 2
• 239000002026 chloroform extract Substances 0.000 description 2
• 238000000605 extraction Methods 0.000 description 2
• 238000002955 isolation Methods 0.000 description 2
• 229940098779 methanesulfonic acid Drugs 0.000 description 2
• LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
• GANBJDIOIDQSGI-UHFFFAOYSA-N 2-(chloromethyl)furan Chemical compound ClCC1=CC=CO1 GANBJDIOIDQSGI-UHFFFAOYSA-N 0.000 description 1
• WECUIJXZKLGURU-UHFFFAOYSA-N 3-(chloromethyl)furan Chemical compound ClCC=1C=COC=1 WECUIJXZKLGURU-UHFFFAOYSA-N 0.000 description 1
• QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
• 230000002378 acidificating effect Effects 0.000 description 1
• 150000003863 ammonium salts Chemical class 0.000 description 1
• 125000004432 carbon atom Chemical group C* 0.000 description 1
• 239000007795 chemical reaction product Substances 0.000 description 1
• 238000001816 cooling Methods 0.000 description 1
• 238000002425 crystallisation Methods 0.000 description 1
• 230000008025 crystallization Effects 0.000 description 1
• 230000000694 effects Effects 0.000 description 1
• 239000000284 extract Substances 0.000 description 1
• YKASHPSKFYVZRC-UHFFFAOYSA-M furan-2-ylmethyl(trimethyl)azanium;iodide Chemical compound [I-].C[N+](C)(C)CC1=CC=CO1 YKASHPSKFYVZRC-UHFFFAOYSA-M 0.000 description 1
• 229910052736 halogen Inorganic materials 0.000 description 1
• 150000002367 halogens Chemical group 0.000 description 1
• 239000012442 inert solvent Substances 0.000 description 1
• 239000013067 intermediate product Substances 0.000 description 1
• 230000007935 neutral effect Effects 0.000 description 1
• TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
• 230000020477 pH reduction Effects 0.000 description 1
• 239000000047 product Substances 0.000 description 1
• 238000000746 purification Methods 0.000 description 1
• 125000001453 quaternary ammonium group Chemical group 0.000 description 1
• 239000002904 solvent Substances 0.000 description 1
• 238000003756 stirring Methods 0.000 description 1
• 150000003512 tertiary amines Chemical class 0.000 description 1