PROCESS FOR MANUFACTURE OF HIGH PURITY D-(-)-N,N-DIETHYL-2-(alpha-NAPHTHOXY) PROPIONAMIDE
AssigneeUnited Phosphorus, Ltd.
InventorsJaidev Rajnikant Shroff, Vikram Rajnikant Shroff, Narendra Purushottam Karambelkar
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Abstract
According to one aspect of the present invention there is provided a substantially high purity D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide and a process for the manufacture of substantially higher purity D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide having chemical purity near about or above 95%, and chiral purity near about or more than 97%. According to another aspect of the invention is to provide an agrochemical compositions containing highly pure optically active D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide.
Claims42
1-19. (canceled)
A process for the preparation of D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide comprising:
- (a) reacting (L)-2-(−)halopropionic acid with a chlorinating agent and dimethylformamide to form (L)-2-(+)-halopropionyl chloride;
- (b) reacting the (L)-2-(+)-halopropionyl chloride with diethyl amine in presence of an aqueous solution of alkali metal hydroxide to form (L)-(+)-2-halo-N,N-diethyl propionamide;
- and
- (c) reacting the mass containing (L)-(+)-2-halo-N,N-diethyl propionamide, with α-naphthol in the presence of aqueous alkali metal hydroxide to form D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide.
A process for the preparation of high purity D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide comprising:
- (a) reacting (L)-2-(−)halopropionic acid with a chlorinating agent and dimethylformamide to form (L)-2-(+)-halopropionyl chloride;
- (b) reacting the (L)-2-(+)-halopropionyl chloride with diethyl amine in presence of an aqueous solution of alkali metal hydroxide to form (L)-(+)-2-halo-N,N-diethyl propionamide;
- (c) reacting the mass containing (L)-(+)-2-halo-N,N-diethyl propionamide, with α-naphthol in the presence of aqueous alkali metal hydroxide to form D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide;
- and
- (d) recrystallizing the D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide in a polar organic solvent or polar aqueous organic solvent.
D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide having a chiral purity of at least about 80%.
D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide having a chiral purity of at least about 95%.
D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide having a chiral purity of at least about 98%.
D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide having about 100% chiral purity.
An agrochemical composition comprising D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide having a chiral purity of at least about 80% and agrochemically acceptable excipients.
An agrochemical composition comprising D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide having a chiral purity of about 95% to about 100% and agrochemically acceptable excipients.
An agrochemical dry flowable composition comprising D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide, an alkyl naphthalene sulfonate sodium salt, a styrene acrylic copolymer, silicon dioxide and kaolin, wherein said D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide has an optical purity of at least about 80% to about 100%.
An agrochemical suspension concentrate composition comprising D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide, an alkyl naphthalene sulfonate sodium salt, an α-hydro-ω-hydroxypoly(oxyethylene)poly(oxypropylene)poly(oxyethylene) block copolymer, propylene glycol, silicon emulsion, natural clay, 1,2-benzisothiazolin-3-one and xanthan gum, wherein said D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide has an optical purity of at least about 80% to about 100%.
An agrochemical emulsifiable concentrate composition comprising D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide, a mixture comprising calcium alkylbenzene sulfonate and tristeryl phenol ethoxylate (16 moles) and xylene, wherein said D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide has an optical purity of about 80% to about 100% and a chemical purity of about 95%.
An oil-in-water concentrated emulsion composition comprising D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide, a mixture comprising calcium alkylbenzene sulfonate and tristeryl phenol ethoxylate (16 moles), a solvent selected from xylene or isophorone or combination thereof, xanthan gum and 1,2-benzisothiazolin-3-one, wherein said D-(−)-N,N-diethyl-2-(α-naphthoxy)propionamide has an optical purity of about 80% to about 100%.
Dependencies are inferred from the claim text.