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

HRID 1884818
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HRID 1884818 반응식
[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
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참가 물질

6

반응물 4

HCID 5238Sodium IodideHCID 5327SulfamethazineHCID 8471TriethylamineHCID 124084321H-Benzimidazole, 2-(chloromethyl)-1-ethyl-

생성물 1

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

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-2589bfd48aa7499dbd952b61b4c24db6
출처 데이터셋
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06767909B2

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