Methyltrimethoxysilane (MTM) as a Reagent for Direct Amidation of Carboxylic Acids

DOI: 10.14469/hpc/9991 Metadata

Created: 2021-12-14 15:24

Last modified: 2022-01-09 14:09

Author: Joshua Davies

License: Creative Commons: Public Domain Dedication 1.0

Funding: (none given)

Description

Methyltrimethoxysilane, (MTM, CH3Si(OMe)3) has been demonstrated as an effective, inexpensive and safe reagent for the direct amidation of carboxylic acids with amines. Two simple work-up procedures have been developed that provide the pure amide product without the need for further purification. The first employs an aqueous base mediated annihilation of MTM. A second involves simple product crystallisation from the reaction mixture providing a low process mass intensity direct amidation protocol.

Members

DOIDescription
10.14469/hpc/9992 N-(4-Methylbenzyl)-2-phenylacetamide (3)
10.14469/hpc/9993 1-Morpholino-2-phenylethan-1-one (4)
10.14469/hpc/9994 N-Benzyl-N-methyl-2-phenylacetamide (5)
10.14469/hpc/9995 N-(4-Methylbenzyl)benzamide (6)
10.14469/hpc/9996 Morpholino(phenyl)methanone (7)
10.14469/hpc/9997 N-Methyl-N-benzylbenzamide (8)
10.14469/hpc/10006 N,2-Diphenylacetamide (9)
10.14469/hpc/10008 N-Phenylbenzamide (10)
10.14469/hpc/10009 N-Benzyl-2-phenylacetamide (11)
10.14469/hpc/10010 N-(4-Methylbenzyl)-2-(thiophen-2-yl)acetamide (12)
10.14469/hpc/10011 2-Phenyl-1-(piperidin-1-yl)ethan-1-one (13)
10.14469/hpc/10012 N-Cycloheptylcyclohexanecarboxamide (14)
10.14469/hpc/10013 (S)-N-(1-Phenylethyl)pivalamide (15)
10.14469/hpc/10014 N-Hexyl-4-iodobenzamide (16)
10.14469/hpc/10015 2-Chloro-N-(4-methylbenzyl)benzamide (17)
10.14469/hpc/10016 N-(4-Methylbenzyl)hex-5-ynamide (18)
10.14469/hpc/10017 N-(4-Methylbenzyl)cinnamamide (19)
10.14469/hpc/10018 N-Octyloctanamide (20)
10.14469/hpc/10019 N-(4-Methylbenzyl)nicotinamide (21)
10.14469/hpc/10020 Benzyl (S)-(1-(benzylamino)-1-oxopropan-2-yl)carbamate (22)
10.14469/hpc/10021 tert-Butyl (S)-(1-(benzylamino)-1-oxopropan-2-yl)carbamate (23)
10.14469/hpc/10022 N-(4-Methylbenzyl)ferrocene carboxamide (24)
10.14469/hpc/10023 2-Amino-N-(4-methylbenzyl)benzamide (25)
10.14469/hpc/10024 3-(4-Chlorophenyl)-N-phenylpropanamide (26)
10.14469/hpc/10026 N1,N3-Bis(4-methylbenzyl)malonamide (27)
10.14469/hpc/10027 N-Methoxy-N-methyl-2-phenylacetamide (28)
10.14469/hpc/10028 N-Hexyl-2-hydroxy-2-phenylacetamide (29)
10.14469/hpc/10030 N,N-Diethyl-2-phenylacetamide (30)
10.14469/hpc/10034 N-Phenyl-2-(thiophen-2-yl)acetamide (31)
10.14469/hpc/10035 Benzyl ((S)-1-oxo-1-(((S)-1-phenylethyl)amino)propan-2-yl)carbamate (32)

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