Sodium Carbonate → HCID 35399006, compound

HRID 2220153Notes

Reaction equation

HRID 2220153 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][NH:8][CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.C(=O)([O-])[O-].[Na+].[Na+].[C:17]([C:19]1[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1)#[N:18]>C(Cl)Cl>[O:1]1[C:5]2([CH2:10][CH2:9][N:8]([S:25]([C:22]3[CH:21]=[CH:20][C:19]([C:17]#[N:18])=[CH:24][CH:23]=3)(=[O:27])=[O:26])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 394974-Cyanobenzenesulfonyl chlorideHCID 674351,4-Dioxa-8-azaspiro(4.5)decane

Product 1

HCID 35399006HCID 35399006, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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.

Workup

  1. temperaturecooled to <10° C
  2. temperaturemaintaining the temperature below 10° C. (
  3. additiontypically addition
  4. temperatureCooling
  5. customwas removed
  6. waitcontinued for 2 h
  7. customThe layers were separated
  8. washthe organic layer was washed with water (2×100 ml)
  9. concentrationconcentrated in vacuo to approximately 100 ml
  10. additionHexane (about 300 ml) was added
  11. customcrystallisation
  12. waitThe precipitate was aged at 0-5° C. for 10-30 min
  13. filtrationfiltered
  14. washwashed with hexane (2×100 ml)

Sources & evidence

ORD record
ord-b16f841ab970454499897b2b903d0306
Source dataset
uspto-grants-2008_08
Patent number
US07417058B2

Reaction notes

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