2-(DiMethylaMino)acetaldehyde sulfite Chemical Properties

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

form 

solid

color 

White

InChI

InChI=1S/C4H9NO.H2O3S/c1-5(2)3-4-6;1-4(2)3/h4H,3H2,1-2H3;(H2,1,2,3)

InChIKey

XALXJVVARIGVBA-UHFFFAOYSA-N

SMILES

C(=O)CN(C)C.S(O)(O)=O

Safety Information

HS Code 

2912190090

2-(DiMethylaMino)acetaldehyde sulfite Usage And Synthesis

Uses

2-(Dimethylamino)acetaldehyde sulfite is an intermediate compound that can be used in the preparation of the hallucinogenic compounds psilocin and psilocybin.

Synthesis

The general procedure for synthesizing 2-(dimethylamino)acetal sulfite from dimethylaminoacetaldehyde diethyl acetal was as follows: 40.0 g of dimethylaminoacetaldehyde diethyl acetal was added to a mixture comprising 48.0 g of concentrated hydrochloric acid and 20.0 mL of water, heated to 40°C and maintained at this temperature for 3 hours of reaction. Subsequently, a solution of 42.4 g of sodium bisulfite dissolved in 72.0 mL of water (aqueous sodium bisulfite) was slowly added dropwise, and stirring of the reaction mixture was continued for 1 hour after completion of the dropwise addition. 200.0 mL of ethanol was added to the reaction system and the mixture was subsequently stirred at 0°C for 2 hours. Upon completion of the reaction, the suspension was separated by filtration, and the solid product was washed with 160.0 mL of ethanol and dried under vacuum at 45 °C. A final product of 42.5 g was obtained in 89.6% yield of the theoretical value. The product started to decompose at 180°C.

References

[1] Patent: WO2007/85638, 2007, A1. Location in patent: Page/Page column 23