Sodium Iodide → n-(4,6-Dimethylpyrimidin-2-yl)-4-[(1-ethyl-1h-benzimidazol-2-ylmethyl)-amino]-benzenesulfonamide

HRID 1884818Notes

Reaction equation

HRID 1884818 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]([N:22]1[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=2[N:24]=[C:23]1[CH2:31]Cl)[CH3:21].C(N(CC)CC)C.[I-].[Na+]>CO>[CH3:1][C:2]1[CH:3]=[C:4]([CH3:19])[N:5]=[C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([NH:18][CH2:31][C:23]3[N:22]([CH2:20][CH3:21])[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[N:24]=3)=[CH:14][CH:13]=2)(=[O:11])=[O:10])[N:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 5327SulfamethazineHCID 8471TriethylamineHCID 12408432HCID 12408432, compound

Product 1

HCID 9954705n-(4,6-Dimethylpyrimidin-2-yl)-4-[(1-ethyl-1h-benzimidazol-2-ylmethyl)-amino]-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

32.4 mg (0,12 mmol) sulfamethazine and 36 mg (0.18 mmol) 1-ethyl-2-chloromethylbenzimidazole were dissolved in 4 ml methanol. 64 μl (0.44 mmol) triethylamine and catalytic amount of sodium iodide were added to the reaction mixture. Solution was stirred and refluxed overnight. The reaction mixture was then evaporated to dryness, and purified on silica using gradient elution (chloroform to 5% methanol in chloroform) to provide white crystals of the title compound, 10 mg (20%). 1H NMR (DMSO-d6, 500 MHz): 7.68 (2H, m), 7.60 (1H, m), 7.52 (1H, m), 7.22 (1H, m), 7.17 (1H, m), 7.00 (1H, br, s), 6.78 (3H, m), 6.60 (1H, br, s), 4.60 (2H, m), 4.30 (2H, q, 7.2 Hz), 2.18 (6H, s), 1.28 (3H, t, 7.2 Hz); MS (ESI+): m/z 437 (M+H)+.

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture was then evaporated to dryness
  3. custompurified on silica using gradient elution (chloroform to 5% methanol in chloroform)

Sources & evidence

ORD record
ord-2589bfd48aa7499dbd952b61b4c24db6
Source dataset
uspto-grants-2004_07
Patent number
US06767909B2

Reaction notes

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