Sodium Carbonate → HCID 35399006, compound

Participants

Reaction Steps

1,4-dioxa-8-azaspiro(4,5)decane (20.0 g, 0.14 mol), DCM (300 ml) and 1N aqueous sodium carbonate solution (200 ml) were charged to a flask and cooled to <10° C. A solution of 4-cyanobenzenesulfonyl chloride (26.8 g, 0.133 mol) in DCM (100 ml) was added dropwise, maintaining the temperature below 10° C. (typically addition takes 40-50 min). Cooling was removed and stirring at room temp continued for 2 h. The layers were separated, the organic layer was washed with water (2×100 ml) and concentrated in vacuo to approximately 100 ml. Hexane (about 300 ml) was added to initialise crystallisation. The precipitate was aged at 0-5° C. for 10-30 min, filtered and washed with hexane (2×100 ml) to yield 38.2 g (88%) of 4-(1,4-dioxa-8-azaspiro[4.5]dec-8-ylsulfonyl)benzonitrile 7a as white solid.

Provenance & Evidence