Sulfamethazine → HCID 23504900, compound

HRID 1884823

Reaction equation

HRID 1884823 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([OH:12])=O.[CH3:13][C:14]1[CH:15]=[C:16]([CH3:31])[N:17]=[C:18]([NH:20][S:21]([C:24]2[CH:25]=[CH:26][C:27]([NH2:30])=[CH:28][CH:29]=2)(=[O:23])=[O:22])[N:19]=1.C(N(CC)CC)C.C(N=C=NC(C)C)(C)C>C(Cl)(Cl)Cl>[CH3:31][C:16]1[CH:15]=[C:14]([CH3:13])[N:19]=[C:18]([NH:20][S:21]([C:24]2[CH:25]=[CH:26][C:27]([NH:30][C:10](=[O:12])[CH2:9][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[O:2][CH3:1])=[CH:28][CH:29]=2)(=[O:23])=[O:22])[N:17]=1

Participants

6

Reactant 4

HCID 5327SulfamethazineHCID 71342-Methoxyphenylacetic acidHCID 8471TriethylamineHCID 12734Diisopropylcarbodiimide

Product 1

HCID 23504900HCID 23504900, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Methoxyphenylacetic acid (33 mg, 0.20 mmol) and sulfamethazine (55 mg, 0.20 mmol) were dissolved in 4 ml of chloroform. Triethylamine (70 μl, 0.55 mmol) and diisopropylcarbodiimide (50 μl, 0.20 mmol) were added to the reaction mixture. Solution was stirred and refluxed overnight. The reaction mixture was then evaporated to dryness, washed with water and purified on silica using gradient elution (chloroform to 2% methanol in chloroform) to obtain white crystals with the yield of 40%. 1H NMR (CDCl3, 500 MHz): 8.04 (2H, m), 7.54 (2H, m), 7.30 (2H, m), 6.98 (2H, m), 6.60 (1H, s), 3.95 (3H, s), 3.72 (2H, s), 2.33 (6H, s); MS (ESI+): m/z 449 (M+Na)+, 427 (M+H)+.

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture was then evaporated to dryness
  3. washwashed with water
  4. custompurified on silica using gradient elution (chloroform to 2% methanol in chloroform)
  5. customto obtain white crystals with the yield of 40%

Sources & evidence

ORD record
ord-433da962c43a4fbf8a0b104ef2722b91
Source dataset
uspto-grants-2004_07
Patent number
US06767909B2

Linked notes

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