N-Acetylsulfanilyl chloride → N-(4-{[3-(morpholin-4-yl)propyl]sulfamoyl}phenyl)acetamide

HRID 215755Notes

Reaction equation

HRID 215755 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][CH2:9][NH2:10])[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].[C:17]([NH:20][C:21]1[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1)(=[O:19])[CH3:18]>CC(C)=O.O>[C:17]([NH:20][C:21]1[CH:22]=[CH:23][C:24]([S:27]([NH:10][CH2:9][CH2:8][CH2:7][N:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)(=[O:29])=[O:28])=[CH:25][CH:26]=1)(=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 8481N-Acetylsulfanilyl chlorideHCID 11430Potassium CarbonateHCID 61055N-(3-Aminopropyl)morpholine

Product 1

HCID 2144799N-(4-{[3-(morpholin-4-yl)propyl]sulfamoyl}phenyl)acetamideYield 62%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of 2.8 g (0.020 mol) of 3-morpholinopropylamine in 15 ml of acetone, the solution of 3.3 g (0.024 mol) of potassium carbonate in 3 ml of water was added under stirring. To this mixture, 5 g (0.021 mol) of 4-acetamidobenzenesulphonyl chloride XII was added portionwise at the room temperature for 15 min. The mixture was then stirred at the room temperature for another 2 hours. One half of the solvent volume was distilled off from the mixture, the mixture was cooled to 0° C., Obtained solid was separated, washed 3 times with 5 ml of ice water and dried. Afforded 4.2 g (62%) of 4-acetamido-N-(3-morpholinopropyl)benzenesulphonamide XIII, colourless solid, m.p. 97-98° C.

Workup

  1. stirringThe mixture was then stirred at the room temperature for another 2 hours
  2. distillationOne half of the solvent volume was distilled off from the mixture
  3. customObtained solid
  4. customwas separated
  5. washwashed 3 times with 5 ml of ice water
  6. customdried

Sources & evidence

ORD record
ord-3dbe52c20a23496593af253c0ba69a6d
Source dataset
uspto-grants-2012_06
Patent number
US08193184B2

Reaction notes

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