Reaktion #1117642

Reaktionsgleichung

NAD+

thiophosgene

sodium carbonate

→

NAD NCS

Lösungsmittel

H2O

CHCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewith attached bubble-counter
2. 2
   workup.ADDITIONa little Na2CO3 was added
3. 3
   workup.WAITAfter 3.5 hours there was no longer
4. 4
   SonstigeThe mixture was evaporated to dryness in vacuo
5. 5
   Sonstigefreeze-dried
6. 6
   SonstigeThe slightly brownish product mixture could be purified of by-products by column chromatography on silica gel
7. 7
   Sonstigeunpurified for the reaction with the polymer (see Example 2)
8. 8
   Filtrationsince purification by ultrafiltration of the product

Vorschrift

2 mmol of NAD+ were dissolved in 10 ml of H2O in a round-bottomed flask with attached bubble-counter, and a little Na2CO3 was added. A solution of 20 mmol of thiophosgene in 10 ml of CHCl3 was added with vigorous stirring at 20° C. The pH was checked every 10 minutes and kept between 5.5 and 8.5 by the addition of small amounts of sodium carbonate. After 3.5 hours there was no longer any change in the pH, and no further gas was evolved. The mixture was evaporated to dryness in vacuo and freeze-dried. The slightly brownish product mixture could be purified of by-products by column chromatography on silica gel using water/acetonitrile as eluent. However, it is advisable to use the product mixture unpurified for the reaction with the polymer (see Example 2), since purification by ultrafiltration of the product immobilized on the polymer is considerably more straightforward and, moreover, the sensitivity of NAD-NCS results in losses due to dimerization and trimerization during purification.

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