N-[4-(6-chloro-2-ethylamino-pyrimidin-4-ylsulfamoyl)-phenyl]-acetamide → 4-amino-N-(6-chloro-2-ethylamino-pyrimidin-4-yl)-benzenesulfonamide

HRID 378271Notes

Reaction equation

HRID 378271 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[N:5]=[C:4]([NH:11][S:12]([C:15]2[CH:20]=[CH:19][C:18]([NH:21]C(=O)C)=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:3]=1>[OH-].[Na+]>[NH2:21][C:18]1[CH:19]=[CH:20][C:15]([S:12]([NH:11][C:4]2[CH:3]=[C:2]([Cl:1])[N:7]=[C:6]([NH:8][CH2:9][CH3:10])[N:5]=2)(=[O:13])=[O:14])=[CH:16][CH:17]=1

Participants

3

Reactant 1

HCID 10809139N-[4-(6-chloro-2-ethylamino-pyrimidin-4-ylsulfamoyl)-phenyl]-acetamide

Product 1

HCID 108300934-amino-N-(6-chloro-2-ethylamino-pyrimidin-4-yl)-benzenesulfonamideYield 90%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2.88 g (0.0075 mol) of N-[4-(6-chloro-2-ethylamino-pyrimidin-4-ylsulfamoyl)-phenyl]-acetamide were dissolved in 76 ml of 1N NaOH and boiled at reflux for 3 hours. The mixture was extracted with ethyl acetate, the aqueous phase was saturated with sodium chloride and the residual ethyl acetate was distilled on a rotary evaporator. Then, the aqueous phase was made acid with 3N HCl and the precipitate which separated was filtered off under suction. After drying there were obtained 2.2 g (90%) of 4-amino-N-(6-chloro-2-ethylamino-pyrimidin-4-yl)-benzenesulfonamide as white crystals; m.p.: 172-173° C.

Workup

  1. temperatureat reflux for 3 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. distillationthe residual ethyl acetate was distilled on a rotary evaporator
  4. customthe precipitate which separated
  5. filtrationwas filtered off under suction
  6. customAfter drying there

Sources & evidence

ORD record
ord-aab7e5883ba04926a303d84de4122597
Source dataset
uspto-grants-2000_02
Patent number
US06030976

Reaction notes

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