Dichloro-acetamide

Chemical Name D(-)-threo-2,2-dichloro-N- [/3 hydroxy-a-(hydroxymethyl)-p-nitrophenethyl] -acetamide... 

CN [/ -(/ , / )]-2,2-dichloro-N-[2-hydroxy-]-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide... 

The inclusion of aromatic rings as part of the side chains results in quite potent agents, possibly because the rigid rings better define the position of the basic nitrogen. Reaction of para-hydroxyacetanilide (19-1) with formaldehyde and diethylamine affords the corresponding Mannich product (19-2) hydrolysis of the acetamide then leads to the aniline (19-3). Treatment of that compound with dichloro-quinoline (17-6) leads to the displacement of chlorine on the heterocyclic ring and the formation of amodiaquine (19-4) [21]. 

Preparation of A,-[2, 4 -dichloro-5-( 2-[(5-cyanopyridin-2-yl)amino]ethyl -amino)-1,l -biphenyl-2-yl]acetamide... 

SYNS CAP-P CAP-PALMITATE CHLORA.MPHENICOLMONOPALMITATE DETREOPAL o-ESTER PALMITIC ACID with D-threo-(-)-2,2-DICHLORO-N-(P-HYDROXY-a-(HYDROXY-METHYL)-p-NITROPHENETHYL)ACETAMIDE... 

C5H10CI2 1,1 -dichloro-2-methylbutane 23010-05-1 400.00 34.500 2 5425 C5H10N2O2 N-nitroso-N-propyl acetamide 67809-15-8 475.82 41.565 2... 

Compound 77, a simple acetamide analogue with an unsubstituted phenyl group, had nM D3 affinity moreover, replacement of the acetamide with a cyclohexylcarboxamide led to compound 78 with sub-nM potency for the D3 receptor and over 270-fold selectivity for D3 vs D2 receptors. Substitution of the phenyl ring with 2,3-dichloro substitution resulted in compound 79 with decreased D3 affinity and selectivity. 

Polyamine chain extension, 48-56 by acrylamide 51, 52. 53 by aziridine 48,49 by l-bromo-3-chloropropane, 55 by (2-bromoethyl)phthalimide, 51 by 3-bromopropylphthalimide, 53 by chloroacetonitrilc, 51 by chloroacetyl chloride. 50 by lV-(2-chloroethyl)acetamide, 52 by derivatives of chloroacetic acid. 50 by dichloro(o)-bromoalkyl)boranes. 56 by IV-ethylchloroacetamide, 52 by 3-phthalimidopropyl tosylate, 54 by /V-tosyl-2-bromoethylamine, 49 by 2-(N-tosylamino)ethyl tosylate. 49 by Af-tosylaminoacetyl chloride, 50 Polyamino diols. 59 Polyaza-crown macrocycles. 349-367 alkyl-substituted. 364.365 from bis-sulfonamides, 358-361 from diacid dichlorides, 352-357 from diesters, 352-357 from dihalides, 362-366 from diols, 366 from ditosylates. 362-366 Polyaza-crown macrocycles (miscellaneous), table. 392... 

Beilstein Handbook Reference) Acet-amide, 2,2-dichloro-N,N-di-2-propenyl- Acetamide, N,N-diallyl-2,2-dichloro- BRN 1768843 Compound R-25788 Dichlormid 2,2-Dichloro-N,N-di-2-propenyl-acetamide EINECS 253-658-8 N,N-Diallyl-2,2-dichloroacetamlde N,N-Oiallyldichloroacetamide R-25788 Stauffer R-25788. 

C2-homologizati on of sugars with, 264-265 Acetamide, JV-bromo- (AcNHBr, NBA) bromohydrination with, 275-276, 287 Acetaminophen (= paracetamol), 301 Acetate, piperidinium cat. for aldol add., 82 —, sodium a-epimerization of ketones, 277 opening of oxiranes, 282 Acetic acid, anhydride (AcfO) protection with. See Protection Pummerer rearr. with, 51, 265 —, esters (See also Protection of hydroxy groups) C-H acidity, 10 1-methylethenyi ester pr., 174 transenolization, 58 —, bromo-, esters pr., 179 a2-synthon, 19, 65, 309 d2-synthon, 19, 301 —, chloro-, esters pr., 179 hydantoins from, 308 —, cyano-, esters pr., 177 pyrrolines from, 298 —, (dialkoxyphosphinyl)-, esters pr 188 Wittig-Horner olefinations, 267, 282 —, diazo-, ethyl ester pr, 176, 178 cyclopropanes from, 74—75 —, dichloro- deblocking of pixyl ethers, 342 —, hydroxy-, esters pr., 176 —, hydroxyphenyl-, (S)- (l-mandelic acid) ... 

Chloramphenicol 2,2-Dichloro-iV-[1,3-dihydroxy-l -(4-nitrophenyl)propan-2-yl] acetamide C11H12CI2N2O5 OH NH CHCI2 1 T CH2OH 0 N/A ... 

Analogously, a satisfactory yield of IbP was obtained by treating 2,6-dichloro-5-fluoro-3-aminopyridine with substituted acetamide in the presence of oxalyl chloride to give an amidine followed by reaction with potassium carbonate (94HCA1057). 

R = Me, CH2Ph) with tri-n-butyl tin hydride followed by NaBHjCN reduction affords the 7-exo cyclization products (165 R = Me, CHzPh), even if in only poor to moderate yield <9ITL2829>. In a similar reaction, 2,2-dichloro-iV-methyl-iV-(o-allylphenyl)-acetamide furnishes the 1-exo product, 4-methyl-2,3,4,5-tetrahydro-l/7-benz[Z)]azepine (166) in 49% yield <91JCS(P1)353>. The established photo-induced cyclization of chloracetamides has been applied to a synthesis of the azepino[3,4,5-c,ring system isomeric to that of the clavicipitic acids <88SC671>. 

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