Propionyl chloride, 2-chloro

Although geneologically related to indoles, the dihydroindoles behave chemically rather like alkyl anilines. When diphenylamine reacts with chloro-propionyl chloride, amide 40 results this in turn readily cyclizes to oxindole 41. Sodium hydride followed by 2-chloroethyldimethylamine alkylates the 3-position (possibly through an intermediate aziridinium ion) partial demethylation is accomplished by refluxing with ethylchiorocarbonate, followed by hydrolysis of the intermediate carbamate to give indolinone 42, the antidepressant amedalin Repetition of this sequence on the chloropropyl homologue, followed by reduction of the appropriate indolinone produces dihydroindole 43, daledalin, which also has antidepressant activity. ... 

Chloro propionyl chloride pyroquilon Chloro pyruvic acid pyraclofos, thiabendazole... 

The Woodward group employed the reaction in the synthesis of cortisone but used free ethyl vinyl ketone rather than the Mahnich base methiodide. Their improvement of an Ccu-ly preparative procedure is as follows." Fricdel-Crafts reaction of propionyl chloride with ethylene in chloroform affords 1 -chloro-3-pentanone. and when a mixture of this with an equivalent amount of diethylamine is heated gradually lu 200° ethyl vinyl ketone dlHlillx. 

To a solution of phenylsulfinylcyclopropane (3 mmol) in CHjClj (10 mL) was added SOCI2 (or propionyl chloride) (1.2 molar excess) in CHjClj (10 mL). The mixture was kept refluxing for 1 h and then at rt for 2 h. Then, the solution was poured into 5% aq NUjCOj (50 mL) and washed with HjO. The CHjClj layer was dried (MgS04). After removal of CHjClj the resulting 1-chloro-l-phenylsulfanylcyclopropane was purified by distillation in vaeuo. 

Preparation. Owen and Reese1 have developed a convenient method suitable for the large-scale preparation of tetrahydro-4//-pyrane-4-one (3), the precursor of 4-methoxy-5,6-dihydro-2//-pyrane (2,271). Ethylene is acylated with 3-chloro-propionyl chloride (1) in virtually quantitative yield to give l,5-dichloropentane-3-one (2). This is then hydrolyzed with sodium hydrogen phosphate at 90°. 

If propionyl chloride (0.5 mole), S02C12, and iodine (0.5 g) are boiled under reflux for 12 h, the pure 2-chlorbpropionyl chloride (22 g) and none of the 3-chloro isomer is obtained 534... 

Preparative Methods from propionyl chloride and 1,3-thiazo-lidine-2-thione in the presence of triethylamine, or from propionic acid and thiazolidine-2-thione in the presence of triethylamine and 2-chloro- 1-methylpyridinium iodide. Handling, Storage, and Precautions use in a fume hood. 

COCH2CH3 - Preparation by Friedel-Crafts acylation of 4-chloro-2-methylphenol with propionyl chloride in the presence of aluminium chloride at 80-90° for 3 h (quantitative yield) [6966]. 

Obtained by reaction of propionyl chloride with-2-chloro-l,4-dimethoxybenzene in the presence of aluminium chloride in carbon disulfide (50%) [7281],... 

N-TFA-L-prolyl methyl esters have been most frequently used for the separation of diastereoisomers of amino acids [295,296], although other procedures have been suggested for blocking the imino group of Pro using functional groups such as a-chloro-propionyl and a-bromopropionyl. The preparation of the derivatives consists in conversion of amino acids into methyl ester hydrochlorides by the action of methanol and thionyl chloride and subsequent reaction with TFA-L-prolyl chloride in dichloromethane... 

Addition of a polarizing catalyst, e.g., I2, is recommended. Thus 2-chloro-propionyl or -butyryl chloride is prepared by passing dry Cl2 into the boiling acid chloride (30 g) containing a little (0.5 g) iodine until the theoretical increase in weight is achieved.538... 

Obtained (major product) by reaction of propio-nyl chloride with 3-chloro-2-methoxybiphenyl in the presence of aluminium chloride, in mixture with its 4 -propionyl isomer (minor product). Total yield (73%) [7695]. 

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