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Synthese de l'acide acetoxy‐2 trifluoromethyl‐4 benzoique [noyau 14 C‐U] OU “triflusal [noyau 14 C‐U]”
Author(s) -
Noel J. P.,
Pichat L.,
Rimbau V.,
Forn J.
Publication year - 1982
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580190309
Subject(s) - chemistry , trifluoromethyl , medicinal chemistry , yield (engineering) , ring (chemistry) , aniline , dichloromethane , phenol , benzene , organic chemistry , solvent , alkyl , materials science , metallurgy
Synthesis of 2‐acetoxy 4‐trifluoromethyl benzoīc acid [ring U ‐ 14 C] or “[ring U‐ 14 C] Trifusal” U14C)(Ring U‐ 14 C) Aniline 1 was converted into (ring U‐ 14 C) idobenzene 2 through the (ring U‐ 14 C) phenyldiazonium chloride. Trifluoromethylation of 2 with iodotrifluoromethane in presence of copper gave (ring U‐ 14 C) trifluoromethylbenzene 3 with a 64% yield. Nitration of 3 with sodium nitrate + trifluoromethane sulfonic acid in dichloromethane gave a 86% yield of (ring U‐ 14 C) 3‐nitro trifluoromethyl benzene 4 which was reduced by iron and HCl into the corresponding amine 5 . The latter was transformed into the phenol 6 with a 85% yield by action of Cu (NO 3 ) 2 and CuO on (ring U‐ 14 C) 3‐trifluo romethyl phenyldiazonium sulfate. Kolbe reaction of phenol 6 with carbon dioxide and K 2 CO 3 gave 7 with a 59% yield. Acetylation of 7 gave (ring U‐ 14 C) Triflusal 8 with a quantitative yield and a specific activity of 14 mCi/mMole 14 radiochemical purity 98.5%. The overall yield from 14 C barium carbonate was 10%.