Approach to green chemistry of DMT-MM: recovery and recycle of coproduct to chloromethane-free DMT-MM

被引：39

作者：

Kunishima, M ^{[1
]}

Hioki, K

Wada, A

Kobayashi, H

Tani, S

机构：

[1] Kobe Gakuin Univ, Fac Pharmaceut Sci, Nishi Ku, Kobe, Hyogo 6512180, Japan

[2] Kobe Gakuin Univ, High Technol Res Ctr, Nishi Ku, Kobe, Hyogo 6512180, Japan

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 18期

关键词：

triazines; condensation; amides;

D O I：

10.1016/S0040-4039(02)00546-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A simple procedure for the isolation of 2-hydroxy-4,6-dimethoxy-1,3,5-triazine (HO-DMT), a coproduct arising from dehydrating condensation using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) has been established. HO-DMT can be recycled by treatment with POCI3 to give 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT), which is further converted to DMT-MM. Alternatively, reaction with traflic anhydride followed by addition of N-methylmorpholine gives DMT-MM triflate. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

收藏

页码：3323 / 3326

页数：4

相关论文

共 13 条

[1] An easy and convenient synthesis of Weinreb amides and hydroxamates [J].

De Luca, L ;

Giacomelli, G ;

Taddei, M .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (07) :2534-2537

[2] PERFLUOROALKYL DERIVATIVES OF SULPHUR .7. ALKYL TRIFLUOROMETHANESULPHONATES AS ALKYLATING AGENTS, TRIFLUOROMETHANESULPHONIC ANHYDRIDE AS A PROMOTER FOR ESTERIFICATION, AND SOME REACTIONS OF TRIFLUOROMETHANESULPHONIC ACID [J].

GRAMSTAD, T ;

HASZELDINE, RN .

JOURNAL OF THE CHEMICAL SOCIETY, 1957, (SEP) :4069-4079

[3] PERFLUOROALKYL DERIVATIVES OF SULPHUR .1. TRIFLUOROMETHANESULPHONIC ACID [J].

HASZELDINE, RN ;

KIDD, JM .

JOURNAL OF THE CHEMICAL SOCIETY, 1954, (DEC) :4228-4232

[4] Benzyl 4,6-dimethoxy-1,3,5-triazinyl carbonate as N-protecting reagent [J].

Hioki, K ;

Fujiwara, M ;

Tani, S ;

Kunishima, M .

CHEMISTRY LETTERS, 2002, (01) :66-67

[5]

Kaminska JE, 1999, SYNTHESIS-STUTTGART, P593

[6] 2-CHLORO-4,6-DISUBSTITUTED-1,3,5-TRIAZINES - A NOVEL GROUP OF CONDENSING REAGENTS [J].

KAMINSKI, ZJ .

TETRAHEDRON LETTERS, 1985, 26 (24) :2901-2904

[7]

KAMINSKI ZJ, 1994, INT J PEPT PROT RES, V43, P312

[8] Cyclodextrin-based artificial acyltransferase: Substrate-specific catalytic amidation of carboxylic acids in aqueous solvent [J].

Kunishima, M ;

Yoshimura, K ;

Morigaki, H ;

Kawamata, R ;

Terao, K ;

Tani, S .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2001, 123 (43) :10760-10761

[9] 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium chloride: An efficient condensing agent leading to the formation of amides and esters [J].

Kunishima, M ;

Kawachi, C ;

Morita, J ;

Terao, K ;

Iwasaki, F ;

Tani, S .

TETRAHEDRON, 1999, 55 (46) :13159-13170

[10] Synthesis and characterization of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride [J].

Kunishima, M ;

Kawachi, C ;

Iwasaki, F ;

Terao, K ;

Tani, S .

TETRAHEDRON LETTERS, 1999, 40 (29) :5327-5330