Abstract
A simple, cost effective and environmentally benign method is reported for the preparation of N,N-dimethylamides from carboxylic acids. The versatility of the method is determined by synthesising a large number of N,N-dimethyl-amide derivatives. Carboxylic acids are heated at 160–165 °C in N,N-dimethylacetamide solvent in the presence of 1,1′-carbonyldiimidazole to afford the corresponding N,N-dimethylamides in good to excellent yields.
References
1.
Coppinger
G.M.
, J. Am. Chem. Soc. , 1954 , 76 , 1372 .
2.
Bosshard
H.H.
,
Mory
R.
,
Schmidt
M.
, and
Zollinger
H.
, Helv. Chim. Acta , 1959 , 42 , 1653 .
3.
Le
J.I.
, and
Park
H.A.
, Bull. Kor. Chem. Soc. , 2001 , 22 , 421 .
4.
Guobin
R.A.
, Chin. J. Org. Chem. , 1996 , 16 , 68 .
5.
Kumagai
T.
,
Anki
T.
,
Ebi
T.
,
Konishi
A.
,
Matsumoto
K.
,
Kurata
H.
,
Kubo
T.
,
Katsumoto
K.
,
Kitamura
C.
, and
Kawase
T.
, Tetrahedron , 2010 , 66 , 8968 .
6.
Kaboudin
B.
, and
Haghighat
H.
, J. Iran. Chem. Soc. 2012 (in press).
7.
Xavier
M.T.
,
Julien
B.
,
Thomas
R.
,
Jordi
S.
,
Jean
M.
, and
Frederic
L.
, Chem. Commun. , 2012 , 48 , 11781 .
8.
Sawant
D.N.
,
Wagh
Y.S.
,
Bhatte
K.D.
, and
Bhanage
B.M.
, J. Org. Chem. , 2011 , 76 , 5489 .
9.
Denmark
S.E.
, and
Butler
C.R.
, J. Am. Chem. Soc. , 2008 , 130 , 3690 .
10.
Liu
Z.
,
Zhang
J.
,
Chen
S.
,
Shi
E.
,
Xu
Y.
, and
Wan
X.
, Angew. Chem., Int. Ed. , 2012 , 51 , 3232 .
11.
Ishizone
T.
,
Wakabayashi
S.
,
Hirao
A.
, and
Nakahama
S.
, Macromol. , 1991 , 24 , 5015 .
12.
Sunada
Y.
,
Kawakami
H.
,
Imaoka
T.
,
Motoyama
Y.
, and
Nagashima
H.
, Angew. Chem., Int. Ed. , 2009 , 48 , 9511 .
13.
Shaughnessy
K.H.
,
Hamann
B.C.
, and
Hartwig
J.F.
, J. Org. Chem. , 1998 , 63 , 6546 .