Diphenylacetyl chloride

This method is general for chloromethyl ketones. Yields of 75-85% may be obtained using hydrocinnamoyl chloride or diphenylacetyl chloride. 

Benzhydryl 2-methyl-3-indolyl ketone (201) has been prepared by the action of diphenylacetyl chloride on 2-methylindole magnesium iodide. ... 

Esters of diphenylacetic acids with derivatives of ethanol-amine show mainly the antispasmodic component of the atropine complex of biologic activities. As such they find use in treatment of the resolution of various spastic conditions such as, for example, gastrointestinal spasms. The prototype in this series, adiphenine (47), is obtained by treatment of diphenyl acetyl chloride with diethylaminoethanol. A somewhat more complex basic side chain is accessible by an interesting rearrangement. Reductive amination of furfural (42) results in reduction of the heterocyclic ring as well and formation of the aminomethyltetrahydro-furan (43). Treatment of this ether with hydrogen bromide in acetic acid leads to the hydroxypiperidine (45), possibly by the intermediacy of a carbonium ion such as 44. Acylation of the alcohol with diphenylacetyl chloride gives piperidolate (46). ... 

To obtain the free base, 34 g (0.256 mol) of N-ethyl-3-piperidinol and 20 g (0.22 mol) of diphenylacetyl chloride were mixed in 80 cc of isopropanol and the solution was refluxed for 2 hours. The isopropanol was evaporated in vacuo at 30 mm pressure, the residue was dissolved in 150 cc of water and the aqueous solution was extracted several times with ether. The aqueous solution was then neutralized with potassium carbonate and extracted with ether. The ethereal solution was dried over anhydrous potassium carbonate and the ether removed by distillation. The product was then distilled at its boiling point 180° to 181°C at 0.13 mm of mercury whereby 14 g of a clear yellow, viscous liquid was obtained. The nitrogen content for CjiHjjNOj was calculated as 4.33% and the nitrogen content found was 4.21%. 

Oxyphenisatin acetate Diphenylacetic acid chloride Diphenpyramide Thiphenamil HCI Diphenyl acetone Diphenadione Diphenylacetonitrile Doxapram HCI Methadone HCI Diphenylacetyl chloride Piperidolate... 

C 4H, N 86-29-J) see Diisopromine Diphenoxylate Doxapram Fenpiverinium bromide Isopropamide iodide Methadone Normethadone Prozapine diphenylacetyl chloride... 

The pyrido[l,2-tf][l,3,5]triazine-2,4(3//)-dione derivative 89 was obtained in a cycloaddition reaction of diphenyl-methyl isocyanate 90 with 2-pyridyl isocyanate 91 derived from the corresponding acyl azide via Curtius rearrangement <2002ARK438>. Compound 89 was also synthesized by the reaction of diphenylacetyl chloride 118 and picolinyl azide 116a in the presence of triethylamine (Scheme 11) <2002ARK438>. ... 

Diphenylketene has been prepared by action of tripropylamine on diphenylacetyl chloride,2 by treating diphenylchloro-acetyl chloride with granulated zinc,3 and by the action of quinoline on diphenylacetyl chloride.4 It is most conveniently prepared by heating phenylbenzoyldiazomethane—a method first described by Schroeter5 and later used by Staudinger.6... 

Diphenylacetyl chloride has been obtained from diphenyl-acetic acid with phosphorus pentachloride, phosphorus oxychloride and phosphorus pentachloride, and thionyl chloride. It has also been prepared by treatment of diphenylketene with hydrogen chloride. The methods of preparation of diphenylketene have been reviewed in an earlier procedure given in this series. To those cited in the earlier procedure should be added the debromination of a-bromodiphenylacetyl bromide with triphenylphosphine. The procedure above is a modification of that described by Staudinger. ... 

Diphenylacetyl chloride crystallizes best when a seed crystal is added to the cold hexane solution. If, after several hours at 0°, crystallization has not commenced, scratching with a glass rod is sufficient to induce crystallization. 

The checkers found it necessary to recrystallize the diphenylacetyl chloride twice to obtain the reported melting point. 

The following procedure is described in US Patent 2,510,773 To an ice-cold solution of 13.3 grams of 2-diethylaminoethanethiol in 100 cc of dry benzene is slowly added a solution of 23.05 grams of diphenylacetyl chloride in 200 cc of dry benzene. The mixture is stirred 2 hours, then heated to dissolve the fine white solid that is formed. Upon cooling 31.3 grams of 2-diethylaminoethyl diphenylthiolacetate hydrochloride precipitates. It recrystallizes from a mixture of benzene and petroleum ether (BP 60° to 70°C) as rosettes of tiny needles and melts at 129° to 130°C. From a mixture of absolute ethanol and ethyl acetate it recrystallizes as large, almost transparent prisms. 

In a similar manner, diphenylacetyl chloride is treated with tripropylamine in ether to give diphenylketene (83%)/ ... 

Diperoxo-oxohexamethylphosphoramido-molybdenum(Vl), 203-204 Diphenoquinones, 270 Diphenyl, 377 Diphenylacetic acid, 301 Diphenylacetyl chloride, 527 Diphenylacetylene, 51, 117, 276-277, 432, 491... 

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