Sulfanilamide → HCID 68632037, compound

HRID 333126Notes

Reaction equation

HRID 333126 reaction equation
[CH2:1]1[N:8]([CH2:9][CH2:10][N:11]2[CH2:18][C:16](=[O:17])[O:15][C:13](=[O:14])[CH2:12]2)[CH2:7][C:5](=[O:6])[O:4][C:2]1=[O:3].[S:19]([NH2:29])(=[O:28])([C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)=[O:20].[I:30][C:31]1[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][CH:32]=1>CN(C=O)C>[C:5]([CH2:7][N:8]([CH2:1][C:2]([NH:35][C:34]1[CH:36]=[CH:37][C:31]([I:30])=[CH:32][CH:33]=1)=[O:3])[CH2:9][CH2:10][N:11]([CH2:12][C:13](=[O:14])[NH:27][C:24]1[CH:23]=[CH:22][C:21]([S:19](=[O:28])(=[O:20])[NH2:29])=[CH:26][CH:25]=1)[CH2:18][C:16]([OH:15])=[O:17])([OH:4])=[O:6]

Participants

5

Reactant 3

HCID 5333SulfanilamideHCID 108934-IodoanilineHCID 513917Ethylenediaminetetraacetic dianhydride

Product 1

HCID 68632037HCID 68632037, compoundYield 5.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of EDTA dianhydride (256 mg, 1.0 mmol) and sulfanilamide (172 mg, 1.0 mmol) in DMF (10.0 mL) was stirred at room temperature for 4 h. 4-Iodoaniline (219 mg, 1.0 mmol) was added to the reaction mixture and the resulting reaction mixture was stirred at room temperature for at least 12 hours (overnight). The solvent was evaporated under reduced pressure and purified over AmberChrom™ resin eluting with CH3CN/water to give the title compound (35.4 mg, 5.5%) as a white solid. 1H NMR (400 MHz, DMSO) δ 10.41 (brs, 1H), 10.19 (s, 1H), 7.79 (d, J=8.0 Hz, 2H), 7.73 (d, J=8.0 Hz, 2H), 7.61 (d, J=8.8 Hz, 2H), 7.47 (d, J=8.8 Hz, 2H), 7.24 (s, 2H), 3.50-3.46 (m, 8H), 2.80 (s, 4H); MS (ESI), 648 (M+H)+.

Workup

  1. customthe resulting reaction mixture
  2. customThe solvent was evaporated under reduced pressure
  3. custompurified over AmberChrom™ resin
  4. washeluting with CH3CN/water

Sources & evidence

ORD record
ord-a89ef191b2274e2f89cb3ce7a3267395
Source dataset
uspto-grants-2014_11
Patent number
US08877970B2

Reaction notes

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