Chloroacetaldehyde → HCID 20213691, compound

A solution of 12.8 ml of monochloroacetaldehyde in 12.8 ml of water was added to a solution of 35.0 g dipotassium 2-nitroethylene 1,1-dithiolate in 225 ml of water, while stirring at room temperature. The reaction mixture was cooled down to 0° C., after which successively 16 ml of concentrated hydrochloric acid and 16 ml of concentrated potassium hydroxide were added, both for 5 minutes; after each addition the reaction mixture was stirred for 5 minutes. Thereafter 13 ml of chloromethylthiocyanate was added in 5 minutes. The reaction mixture was stirred at room temperature during 1.5 hour, and was left to stand overnight. Dichloromethane was added and the reaction mixture was stirred at room temperature during 0.5 hour. After sucking off solid material, the dichloromethane layer was separated and washed with water. The solvent was evaporated and the product was obtained by purification via column chromatography. The desired product was obtained in a yield of 7.1 g; m.p. 86°-87° C.

1. temperatureThe reaction mixture was cooled down to 0° C.
2. additionafter each addition the reaction mixture
3. stirringwas stirred for 5 minutes
4. stirringThe reaction mixture was stirred at room temperature during 1.5 hour
5. waitwas left
6. waitto stand overnight
7. stirringthe reaction mixture was stirred at room temperature during 0.5 hour
8. customthe dichloromethane layer was separated
9. washwashed with water
10. customThe solvent was evaporated
11. customthe product was obtained by purification via column chromatography

ORD record

ord-73cd794be2234f33afa10bc8ce2dfce6

Source dataset

uspto-grants-1987_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04649154