Acetic Acid → 4-[(1H-Benzimidazol-2-ylmethyl)-amino]-N-(pyrimidin-2-yl)-benzenesulfonamide

HRID 1884819Notes

Reaction equation

HRID 1884819 reaction equation
[CH:1]1[CH:2]=[N:3][C:4]([NH:7][S:8]([C:11]2[CH:12]=[CH:13][C:14]([NH2:17])=[CH:15][CH:16]=2)(=[O:10])=[O:9])=[N:5][CH:6]=1.Cl[CH2:19][C:20]1[NH:21][C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=1.C(O)(=O)C>[OH-].[Na+]>[NH:21]1[C:22]2[CH:28]=[CH:27][CH:26]=[CH:25][C:23]=2[N:24]=[C:20]1[CH2:19][NH:17][C:14]1[CH:15]=[CH:16][C:11]([S:8]([NH:7][C:4]2[N:5]=[CH:6][CH:1]=[CH:2][N:3]=2)(=[O:10])=[O:9])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 5215SulfadiazineHCID 785712-Chloromethylbenzimidazole

Product 1

HCID 235049104-[(1H-Benzimidazol-2-ylmethyl)-amino]-N-(pyrimidin-2-yl)-benzenesulfonamideYield 38%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

628 mg (3.8 mmol) sulfadiazine and 728 mg (3.0 mmol) 2-chloromethylbenzimidazole were dissolved in 10 ml 1 M NaOH. Solution was stirred and refluxed for four hours. Reaction mixture was neutralised with addition of 1 M acetic acid until product precipitated. Crystals were filtered and purified on silica using gradient elution (chloroform to 5% methanol in chloroform) to obtain the title compound as white crystals with 38% yield. 1H NMR (DMSO-d6, 500 MHz): 8.46 (2H, m), 7.70 (2H, m) 7.49 (2H, br, m), 7.14 (1H, t, 5.7 Hz) 7.13 (2H, m), 6.98 (1H, m), 6.72 (2H, m), 4.53 (2H, 5.7 Hz); MS (ESI+): m/z 381 (M+H)+.

Workup

  1. temperaturerefluxed for four hours
  2. customReaction mixture
  3. customprecipitated
  4. filtrationCrystals were filtered
  5. custompurified on silica using gradient elution (chloroform to 5% methanol in chloroform)

Sources & evidence

ORD record
ord-9722df6db2814dfe8388c8ad5bbd1407
Source dataset
uspto-grants-2004_07
Patent number
US06767909B2

Reaction notes

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