Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Patent
1999-10-12
2000-10-24
Barts, Samuel
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C07C20900
Patent
active
061370096
ABSTRACT:
The invention is a process to manufacture the intermediate secondary amine N-ethyl-2-chloro-6-fluoro-benzylamine, and then the process of reacting this intermediate to manufacture the herbicide flumetralin. Equimolar quantities of monoethylamine, sodium hydroxide, and 2-chloro-6-fluorobenzyl chloride are reacted at a temperature between about 70.degree. C. and about 100.degree. C. in a composition containing at least 2.5 times the required quantity of monoethylamine. The reagent monoethylamine functions as solvent and heat sink for the reaction, and also minimizes the formation of undesired byproducts. The excess monoethylamine is removed after formation of the intermediate. Then, equimolar quantities of sodium hydroxide in water and molten 4-chloro-3-5-dinitrobenzotrifluoride are added to the intermediate, and the temperature is controlled between about 90.degree. C. and about 115.degree. C. The product of this reaction is relatively pure, i.e., 98 percent by weight, molten flumetralin. It is advantageous to wash the product with boiling water to facilitate removal of salt and excess sodium hydroxide.
REFERENCES:
patent: 3686230 (1972-08-01), Maravetz
patent: 4046809 (1977-09-01), Wilcox
patent: 4169721 (1979-10-01), Wilcox
Emerson, W.S., "The Preparation of Amines by Reductive Alkylation", Organic Reactions 4:174-255 (1948).
Golinski Miroslaw
Kwiatkowski Stefan
Mobley Steven G.
Pupek Kryzsztof
Smith Paul D.
Barts Samuel
SRM Chemical, Ltd. Co.
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