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

HRID 378265Notes

Reaction equation

HRID 378265 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH3:9])[N:5]=[C:4]([NH:10][S:11]([C:14]2[CH:19]=[CH:18][C:17]([NH:20]C(=O)C)=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:3]=1>[OH-].[Na+]>[ClH:1].[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([S:11]([NH:10][C:4]2[CH:3]=[C:2]([Cl:1])[N:7]=[C:6]([NH:8][CH3:9])[N:5]=2)(=[O:12])=[O:13])=[CH:15][CH:16]=1

Participants

3

Reactant 1

HCID 10808139N-[4-(6-chloro-2-methylamino-pyrimidin-4-ylsulfamoyl)-phenyl]-acetamide

Product 1

HCID 193535074-amino-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide hydrochlorideYield 151.3%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

2.7 g (0.008 mol) of N-[4-(6-chloro-2-methylamino-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 off 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 2.12 g (89%) of 4-amino-N-(6-chloro-2-methylamino-pyrimidin-4-yl)-benzenesulfonamide hydrochloride (1:1.9) as white crystals; MS (ISN): me/e=312 (C11H11ClN5O2S-).

Workup

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

Sources & evidence

ORD record
ord-0ab3b0b6e90945008ac59087663769d3
Source dataset
uspto-grants-2000_02
Patent number
US06030976

Reaction notes

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