N-Acetylsulfanilyl chloride → HCID 13537215, compound

HRID 235659Notes

Reaction equation

HRID 235659 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[NH2:21][CH2:22][CH:23]1[CH2:27][CH2:26][CH2:25][N:24]1[CH2:28][CH3:29]>C(Cl)(Cl)Cl>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:21][CH2:22][CH:23]2[CH2:27][CH2:26][CH2:25][N:24]2[CH2:28][CH3:29])(=[O:13])=[O:12])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8481N-Acetylsulfanilyl chlorideHCID 10340Sodium CarbonateHCID 1172952-Aminomethyl-1-ethylpyrrolidine

Product 1

HCID 13537215HCID 13537215, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Acetylaminobenzenesulphonyl chloride (7.3 g, 0.03 mol) was added portionwise to a well stirred mixture of aqueous sodium carbonate (21.2 g. in 250 ml of water) and 2-aminomethyl-1-ethylpyrrolidine (4.0 g. 0.03 mol) in chloroform (250 ml) at about 10°. The ice bath used for cooling was removed. After 2 hours the chloroform layer was separated, dried (MgSO4) and then evaporated under reduced pressure to give a gum, which slowly crystallised (11.6 g). Recrystallisation from cold ethanol, followed by recrystallisation from water gave the pure title compound m.p. 94°-96° C..

Workup

  1. temperaturefor cooling
  2. customwas removed
  3. customAfter 2 hours the chloroform layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customto give a gum, which
  7. customslowly crystallised (11.6 g)
  8. customRecrystallisation from cold ethanol
  9. customfollowed by recrystallisation from water

Sources & evidence

ORD record
ord-b3a91e91bf804c118d43e133155581fa
Source dataset
uspto-grants-1987_02
Patent number
US04640920

Reaction notes

Loading…