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ChemicalBook CAS DataBase List CHLORANOCRYL
2164-09-2

CHLORANOCRYL synthesis

3synthesis methods
Chloranocryl is produced through a multi step chemical synthesis typical of anilide herbicides. According to the synthesis data, the process begins with 3,4 dichloroaniline, which is reacted with methacryloyl chloride in a cooled polar solvent such as dimethylacetamide, with the temperature kept below 0 DegC to control reactivity. The mixture is then stirred at ambient temperature for an extended period to complete acylation, forming the key intermediate 3,4 dichloro N methacryloyl aniline. This intermediate is subsequently converted into the final herbicidal structure through additional steps involving epoxy acyl intermediates and solvent based purification.
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Yield:-

Reaction Conditions:

in ISOPROPYLAMIDE;toluene;Petroleum ether

Steps:

3 EXAMPLE 3
The 3,4-dichloro-N-(2,3-epoxy-2-methylpropionyl)aniline used as starting material was obtained as follows: A solution of 3,4-dichloroaniline (10 g.) in dimethylacetamide (25 ml.) was added dropwise to a stirred, cooled solution of methacryloyl chloride (10 ml.) in dimethylacetamide (50 ml.) at such a rate that the internal temperature of the mixture did not exceed 0° C., and the mixture was then stirred at laboratory temperature for 16 hours and then poured into cold water (1 liter). The mixture was extracted 5 times with diethyl ether (100 ml. each time) and the combined extracts were dried and evaporated to dryness. The residue was crystallized from a 1:1 v/v mixture of toluene and petroleum ether (b.p. 60°-80° C.) at -50° C., and there was thus obtained 3,4-dichloro-N-methacryloylaniline, m.p. 120°-122° C.

References:

Imperial Chemical Industries PLC US4636505, 1987, A

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