DMF*S03 complex is a unique agent for sulfating and amide preparation

DMF*S03 sulfation agents are an ideal source of S03 for various reactions

° Stable in storage • Easily prepared ο Easily controlled in reactions • Titratable to determine SO3 content

High substitution of polysaccharides without degradation The disadvantages of common methods of making cellu­lose sulfates have been overcome by using DMF*S03 com­plex. Sulfation of cellulose at low temperature with high degree of substitution was achieved through the use of DMF»S03 complex (Chemistry and Industry, 5/28/66,900).

Degrees of substitution of 2.6 to 2.7 were achieved on wood, cellulose and cotton linters by sulfating with DMF «S03 complex at 5°C for three hours. Preparation of polypeptides with DMF-S03 The use of DMF and DMF-S03 overcomes many difficulties usually associatedwith polypeptide syntheses. Mixed anhy­drides containing the COOSO3 group were prepared using DMF*S03 complex. It was reported (U.S. patent 2,766,225) that high yields were obtained from monoamino acids.

- CH -c-o"K r

1 NH I C = 0 I

+ N H j - R " - C 0 0 H

DMF-SQ3

DMF '

R'= R" =

protecting group polypeptide

R - C H - C I 0S03-K+

NH I c=o I R'

R » C H - C - N - R " - C - O H

NH

C = 0 I

Ergine synthesis Certain heterocyclic carboxylic acids are difficult to con­vert to amides. Amides of ergot alkaloid derivatives were prepared in good yields through the use of DMF»S03 com­plex. Diamides were prepared by reacting lysergic acid with lithium hydroxide hydrate in methanol, removing the solvent, redissolving in DMF, chilling, and reacting with the DMF-S03 complex, followed by reaction with a desired amine [J. Org. Chem., 24, 368 (1959)].

COOH COOLi*

LiOH ; H20^ N s MeOH

CH,

DMF» SOi DMF '

R,v

R / ™ CON

Discover the opportunities for improving products and processes with Du Pont DMF

Economy in production-scale use DMF is the least expensive of the "super" (highly dipolar aprotic) solvents-it recently was reduced to 22^ per lb. for bulk quantities. In addition, easy recovery, high con­versions and faster reaction rates result in low use-costs. Versatility in chemical processes DMF is used in the manufacture of a wide range of prod­ucts, involving many classes of organic reactions, often with existing equipment. Efficiency through high yields and pure products Higher conversions and faster reaction rates are often possible with DMF, resulting in higher product yields. Product purity results from reduced by-product contam­ination. Easy recovery DMF can easily be recovered by simple distillation at atmospheric or reduced pressure. High recoveries (up to 99%) not only reduce production costs, but also improve pollution control. Du Pont's new DMF Recovery and Puri­fication Bulletin provides basic data on methods and equipment for recovery of DMF in production operations.

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