4 -Chlor-N- -2-methyl

Man erhalt auf diese Weise z. B. N,4-Dimethyl-anilin, 4-Methylamino-acetophenon, 4-Me-thylamino-benzoesaure-ethylester und 4-Chlor-N-methyl-anilin. 

S-[(4-chlor-phenoxycarbonyl)-methylester]-0,0-diethylester XII/2, 695 S-f(4-chlor-phenoxy)-N-(4-chlor-phenylimino-methyl]- -O.O-diethylester XII/2, 824 S-[N -(4-chlor-phenyl)-N,N-dimethyl-amidino]- -0,0-diethylester XII/2, 824... 

Oxazol 5-(Aminoxy-methyl)-4-chlor-3-methyl- -Hydrochlorid E16a, 228 (N-Deacylier.)... 

Chlor-l-methyl- -methylsulfat E7a, 559 (N-Methylier.) Quinolizinium 4-Chlor-6-methyl- -perchlorat E7a, 793 [4-Oxo —6-CH3-4H-quinolizin + PC13]... 

Triazin 5-[Chlor-(N-methyl-anilino)-methyl]-3-methylthio-E9c, 631 (H - CHQ—NR2)... 

N-Phenyl N [4 chlor 3 methyl phenyl].thio hanutoff 12, 871. 

O, N- Dibenzyl-hydroxylamin 0-Methyl-N-(4-chlor-benzyl)-hydroxylamin... 

N-Diphenylmethylen- 374 N-Diphenylmethylen-O-aminocarbonyl- 612 N-[l,3-Diphenyl-propyl-(2) - 374 N-[l,3-Diphenyl-propyliden-(2)]- 374, 377, 380 N-(4-Halogen-phenyI)- 683 N-Heptyl- 375 N-Heptyl-N-acetyl- 376 N-Heptyliden- 375 N-Hcptyliden-O-acetyl- 376 0-(2-Hydroxy-athyl)-N-athoxycarbonyl- 133 N-(4-Hydroxy-phenyl)- 683 0-(2-Hydroxy-l-phenyl-athyI)-N-athoxycarbonyI-aus 0-(ci-AthoxycarbonyI-benzyl)-N-athoxycar-bonyl-hydroxylamin und Lithiumalanat 133 N-Isopropyl- 682 N-Isopropylidcn- 613 N-Methyl- 133, 682 O-Methyl-N-bcnzyliden- 377 O-Methyl-N-benzyliden- 375 0-Methyl-N-(4-chlor-benzyl)- 375 0-Methyl-N-(4-chlor-benzyliden)- 375 N-Methy -N,0-diacetyI- 682 N-(4-Methyl-phenyl)- 683 0-McthyI-N-( 1 -phenyl-athyliden)- 375 N-(4-Methylthio-phenyl)- 684 N-(4-Nitro-benzyl)- 374 N-[4-Nitro-benzyliden - 374, 377 N-(2-Nitro-phenyl)- 562 N-(4-Nitro-phenyl)- 682 N-Nitroso-N-cyclohexyl- 697 N-Octyl- 374 N-Octyl-(2)-N-acetyl- 376 N-Octyliden- 374 N-0ctyliden-(2)-0-acctyl- 376 N-(Pentafluor-phenyl)-0,N-diacetyl- 697 N-Phenyl- 474, 481, 682, 783 N-Phenylacetyl-O-benzoyl- 265 N-(l-Phenyl-athyl)- 374 N-(l-Phenyl-athyl)-N-acetyl- 376 N-(l-Phenyl-athyliden)-374, 613 N-( l-Phenyl-athyliden)-0-acetyl- 376 N-[ 1 -Phenyl-buten-( 1 )-yl-(3)-iden]- 582 N-f4-Phenyl-butyl-(2)-iden]- 581 N-Phcnyl-N,0-diacetyl- 682 N-(4-Phenylthio-phenyl)- 684 N-Propyl-N-cyclohexyl- 376 N-Propyl-N-isopropyl- 376 O-Sulfonyl- 481 N-(4-Sulfonyl-phenyI)- 683 N-(2-Vinyl-phenyl)- 698... 

N-(4-Chlor-anilinomethyl)- 453 N-(4-Cyan-anilinomethy )- 453 N-(N, 4-Dimethyl-anilinomethyl)- 254 N-Diphcnylmethyl- 255 3 -Hydroxy-N -propyl - 257 N-Methyl-3-benzyl-2-benzyliden- 581 N-Methyl-bis-fbenzylidenJ- 581 N-Methyl-2,3-dibenzyl- 581 N-Phcnyl- 256 N-Pyrrolidinomethyl- 452... 

The oxidation of alcohols to carbonyl compounds has been studied by several authors and a variety of methods have been used. Papers concerned vith such oxidations are illustrated (Scheme 3.26). Good results have been obtained using pyridinium chlor-ochromate (PCC) adsorbed onto silica gel for the selective oxidation of unsaturated substrates e.g. terpene [135] and furanyl derivatives [136]. Steroidal homoallylic alcohols can be converted to the corresponding 4-ene-3,6-diones using tetrapropylammo-nium per-ruthenate (TPAP) in catalytic amounts [137]. In this case, the oxidising agent is N-methyl morpholine N-oxide (NMO). 

Indapamide Indapamide, 4-chloro-N-(2-methyl-l-indolinyl)-3-sulfamoylbenzamide (21.3.33), is synthesized from 2-methylendoline, the nitrosation of which gives 2-methyl-1-nitrosoindoline (21.3.31). Reducing this with lithium aluminum hydride leads to formation of l-amino-2-methylendoline (21.3.32). Acylating this with 3-sulfonylamino-4-chlor-benzoic acid chloride leads to (21.3.33) [53,54]. 

CO —N(C2H5)2 2- (4-Chlor-phenyl) -5-diethylaminocarbonyl-1 -hydroxy-4-methyl-... 56 173... 

Carbonsaure-nitrile konnen mit starken Alkylierungsmitteln [z. B. Trifluor-methansulfonsaure-methylester222,223, Eisen(IIl)-chlorid/2-Chlor-propan224] zu den entsprechenden Nitrilium-Sal-zen umgesetzt werden. Aus N-Methyl-acetnitrilium-trifluormethansulfonat und Diamino-ma-leinsaure-dinitril erhalt man je nach Reaktionsbedingungen 5-Amino-4-aminocarbonyl-l,2-dimethyl-, 5-Amino-4-cyan-l,2-dimethyl- oder 5-Amino-4-(cyan-imino-methyl)-l,2-dimethyl-imid-azol222 223. 

Auch die Reaktion von Azido-benzol und seinen Methyl-, Chlor- und Nitro-Derivaten mit Methyl-benzolen in Gegenwart von Bortrifluorid fuhrt in den meisten Fallen zu Gemischen von aromatischen Aminen, wobei man z.B. aus 4-Azido-l-methyl-benzol und 1,3-Dimethyl-benzol als Hauptprodukt (2,4-Dimethyl-phenyl)-(4-methyl-phenyl)-amin (67%) neben 4-Methyi-N-(3-methyl-benzyl)-anilin (7,5%) und 4-Methyl-anilin (5%) erhalt, aus l-Azido-4-methyl-benzol und Mesitylen jedoch (4- (Methyl-phenyl)-(2,4,6-trime-thyl-phenyl)-amin (55%) neben nur wenig 2,4,6-Trimethyl-anilin (1%)2. 

Durch eine Umlagerung vom Sommelet-Hauser-Typ (vgl. S. 1149) erhalt man beim Erhitzen von N-Aryl-S,S-dimethyl-sulfiliminen in Gegenwart von Triethylamin oder an-deren Basen oder auch Succinimid 2-(Methylthio-methyl)-aniline z. B. 4-Chlor-2-(methylthio-methyl)-anilin (95%)4 bzw. 6-(Methylthio-methyl)-2-trifluormethyl-anilin ( 100%)5 ... 

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