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

HRID 378260Notes

Reaction equation

HRID 378260 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18]C(=O)C)=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[C:4]([Cl:22])[N:3]=1>[OH-].[Na+]>[NH2:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([NH:8][C:6]2[CH:5]=[C:4]([Cl:22])[N:3]=[C:2]([NH2:1])[N:7]=2)(=[O:11])=[O:10])=[CH:13][CH:14]=1

Participants

3

Reactant 1

HCID 10736032N-[4-(2-amino-6-chloropyrimidin-4-ylsulfamoyl)phenyl]-acetamide

Product 1

HCID 107329394-amino-N-(2-amino-6-chloro-pyrimidin-4-yl)-benzenesulfonamideYield 97.5%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

0.885 g (0.0026 mol) of N-[4-(2-amino-6-chloropyrimidin-4-ylsulfamoyl)phenyl]-acetamide was dissolved in 31 ml of 0.5N 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 remaining 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 was obtained 0.76 g (86%) of 4-amino-N-(2-amino-6-chloro-pyrimidine-4-yl)-benzenesulfonamide as beige crystals; m.p.: >265° C. (dec.).

Workup

  1. temperatureat reflux for 3 hours
  2. extractionThe mixture was extracted with ethyl acetate
  3. distillationthe remaining 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-67c2c44d61e04950a8b8fd318843a481
Source dataset
uspto-grants-2000_02
Patent number
US06030976

Reaction notes

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