Mafenide → 2-(3-Acetyl-phenoxy)-N-(4-sulfamoyl-benzyl)-nicotinamide

HRID 844082Notes

Reaction equation

HRID 844082 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH2:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1.[C:13]([C:16]1[CH:17]=[C:18]([CH:29]=[CH:30][CH:31]=1)[O:19][C:20]1[N:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](O)=[O:23])(=[O:15])[CH3:14].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=N)C.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[C:13]([C:16]1[CH:17]=[C:18]([CH:29]=[CH:30][CH:31]=1)[O:19][C:20]1[N:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22]([NH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]([S:9](=[O:10])(=[O:11])[NH2:12])=[CH:7][CH:8]=1)=[O:23])(=[O:15])[CH3:14]

Participants

8

Reactant 5

HCID 3998MafenideHCID 8471TriethylamineHCID 27960291-Hydroxybenzotriazole hydrateHCID 122026462-(3-Acetyl-phenoxy)-nicotinic acidHCID 21883477Ethylcarbodiimide hydrochloride

Product 1

HCID 226120582-(3-Acetyl-phenoxy)-N-(4-sulfamoyl-benzyl)-nicotinamide

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-Aminomethyl-benzenesulfonamide (0.248 grams, 1.11 mmole), 2-(3-Acetyl-phenoxy)-nicotinic acid (0.300 grams, 1.167 mmole), 1-hydroxybenzotriazole hydrate (0.165 grams, 1.22 mmole) and 1-(3-dimethylamino)-propyl)-3-ethylcarbodiimide hydrochloride (0.256 grams, 1.33 mmole) in dimethylformamide (15 ml) was stirred for 10 minutes. To the stirring solution was added triethyl amine (0.280 grams, 2.78 mmole) and stirred over night at room temperature. The mixture was diluted with ethyl acetate and washed with water and brine, dried over MgSO4, filtered and concentrated to give a solid. Recrystalization from ethyl acetate/hexane gave a solid. (0.280 g); M.P.162-164° C.; MS (m/e) 425 (M+).

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give a solid
  6. customRecrystalization from ethyl acetate/hexane
  7. customgave a solid

Sources & evidence

ORD record
ord-4fa41f112620494cb3892363e9c6f8d9
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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