A very convenient dimethylamination of activated aromatic halides using N,N-dimethylformamide and ethanolamines

Tetrahedron Letters

Volumn 38, Issue 48, 1997, Pages 8331-8334

  Cho, Yoon Hwan ^a   Park, Jae Chan ^a  

^a Hanhyo Institute of Technology   (South Korea)

Author keywords

[No Author keywords available]

Indexed keywords

ETHANOLAMINE DERIVATIVE; HALIDE; N,N DIMETHYLFORMAMIDE;

AMINATION; ARTICLE; CHEMICAL REACTION; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0000342939     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)10255-6     Document Type: Article

References (9)

1. (a) Heindel, N; Kennewell, P., J. Chem. Soc. Chem. Commun. 1969, 38.
2. (b) Lord, W.M.; Peters, AT.; J. Chem.Soc.[C], 1968, 783.
3. Coppinger, G.M.; J. Am. Chem. Soc. 1954, 76, 1372.
4. Watanabe, T.; Tanaka, Y.; Sekiya, K.; Akita, Y.; Ohta, A., Synthesis, 1980, 39.
5. (a) Dorigo, P.; Fraccarollo, D.; Santostasi, G.; Maragno, I.; Floreani, M.; Borea, P.; Mosti, L.; Sansebastiano, L.; Fossa, P.; Orsini, F.; Benetollo, F.; Bombieri, G., J. Med. Chem. 1996, 39, 3671.
6. (b) Overberger, C.G.; Kogon, I.C., J. Am. Chem. Soc. 1954, 76, 1065.
7. A typical procedure is as follows: A mixture of PNCB (2.0g, 12.6mmol), diethanolamine (3.37g, 2.5eq.) and DMF(5 ml) was heated to 130°C. After 5.5 hr, the reaction mixture was concentrated under vacuum. Water(30 ml) was added to the residue with stirring. The resulting solids were filtered. At this time excess diethanolamine, byproduct 9 were easily removed because of high water solubility. The solids were washed with ethanol(2 - 3ml) to give bright yellow crystals of 2 (1.80g, 86% yield). M.p. 163.2-164.8°C(lit. 163-164°C)3
8. 1H NMR(300MHz, DMSO d-6)δ 7.97(s, 1H), 4.76 (br, 2H), 3.47(t, 4H), 3.30(m, 4H).
9. Frings, R.B.; Grahe, G.F., Ger. Offen. DE 4042386 A1 920220.