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Radiosynthesis of a chloroacetanilide herbicide ([ phenyl ‐4‐ 3 H] acetochlor) and a dichloroacetamide safener for herbicides ([2, 2‐ dimethyl ‐ 3 H]R‐29148)
Author(s) -
Latli Bachir,
Casida John E.
Publication year - 1995
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.2580360207
Subject(s) - chemistry , acetochlor , triethylamine , medicinal chemistry , acetamide , halogenation , acetone , organic chemistry , nuclear chemistry , pesticide , agronomy , biology
2‐Chloro‐ N ‐(ethoxymethyl)‐ N ‐(2‐ethyl‐6‐methylphenyl)acetamide (the chloroacetanilide herbicide acetochlor) and 3‐(dichloroacetyl)‐ 2,2,5‐trimethyl‐1,3‐oxazolidine (the dichloroacetamide safener R‐ 29148) are required at high specific activity for studies on their metabolism and mode of action. [ phenyl ‐4‐ 3 H]Acetochlor was obtained at 22 Ci/mmol in 71% yield by reductive dehalogenation of iodoacetochlor with tritium gas in ethanol in the presence of palladium on carbon and triethylamine. [2,2‐ dimethyl ‐ 3 H]R‐29148 was prepared at 15 Ci/mmol by treating acetone and 1‐amino‐2‐propanol in pentane with two equivalents of NaOH in tritiated water ( i.e . hydroxide ion‐catalyzed enolization of acetone) followed by dichloroacetyl chloride.