Sulfamethazine → 4-Benzylamino-N-(4,6-dimethylpyrimidin-2-yl)-benzenesulfonamide

HRID 1884821Notes

Reaction equation

HRID 1884821 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH3:19])[N:5]=[C:6]([NH:8][S:9]([C:12]2[CH:13]=[CH:14][C:15]([NH2:18])=[CH:16][CH:17]=2)(=[O:11])=[O:10])[N:7]=1.[CH2:20](Br)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CO>[CH2:20]([NH:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([NH:8][C:6]2[N:5]=[C:4]([CH3:19])[CH:3]=[C:2]([CH3:1])[N:7]=2)(=[O:11])=[O:10])=[CH:13][CH:14]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 5327SulfamethazineHCID 7498Benzyl BromideHCID 10796Cesium carbonate

Product 1

HCID 101558934-Benzylamino-N-(4,6-dimethylpyrimidin-2-yl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

100 mg (0.36 mmol) sulfamethazine and 70.8 μl (0.60 mmol) benzyl bromide were dissolved in 4 ml methanol. Caesium carbonate (113.4 mg, 0.35 mmol) was added and solution was refluxed overnight with stirring. The reaction mixture was then evaporated to dryness, and purified on silica using gradient elution (chloroform to 2% methanol in chloroform) to obtain white crystals in a yield similar to that described in example 1 for step III. 1H NMR (CDCl3, 500 MHz): 7.93 (2H, m), 7.31 (5H, m), 6.58 (3H, m), 4.36 (2H, s), 2.34 (6H, s); MS (ESI+): m/z 369 (M+H)+.

Workup

  1. temperaturesolution was refluxed overnight
  2. customThe reaction mixture was then evaporated to dryness
  3. custompurified on silica using gradient elution (chloroform to 2% methanol in chloroform)
  4. customto obtain white crystals in a yield similar to

Sources & evidence

ORD record
ord-cbdbf0c9d743492b9dc28d251d1b0053
Source dataset
uspto-grants-2004_07
Patent number
US06767909B2

Reaction notes

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