Sodium Carbonate → HCID 62917126, compound

HRID 1677818Notes

Reaction equation

HRID 1677818 reaction equation
[OH:1][CH:2]1[CH2:6][NH:5][CH2:4][CH2:3]1.C(=O)([O-])[O-].[Na+].[Na+].[C:13]([C:15]1[CH:20]=[CH:19][C:18]([S:21](Cl)(=[O:23])=[O:22])=[CH:17][CH:16]=1)#[N:14]>C(Cl)Cl>[OH:1][CH:2]1[CH2:3][CH2:4][N:5]([S:21]([C:18]2[CH:17]=[CH:16][C:15]([C:13]#[N:14])=[CH:20][CH:19]=2)(=[O:23])=[O:22])[CH2:6]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 394974-Cyanobenzenesulfonyl chlorideHCID 982104-Hydroxypyrrolidine

Product 1

HCID 62917126HCID 62917126, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-hydroxypyrrolidine (12 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 drop-wise, maintaining the temperature below 10° C. (typically addition takes 40-50 min). Cooling was removed and stirring at room temperature 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 30.3 g (86%) of sulfonamide 4-[(3-hydroxy-1-pyrrolidinyl)sulfonyl]benzonitrile 23a 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-d818fd2e184249aaa709e1df73d3fe4d
Source dataset
uspto-grants-2011_08
Patent number
US08008341B2

Reaction notes

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