Hydrochloric Acid → 4-Iodo-2-(quinoxaline-5-sulfonylamino)benzoic acid

HRID 2265201Notes

Reaction equation

HRID 2265201 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([I:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[N:12]1[C:21]2[CH:20]=[CH:19][CH:18]=[C:17]([S:22](Cl)(=[O:24])=[O:23])[C:16]=2[N:15]=[CH:14][CH:13]=1.C([O-])([O-])=O.[Na+].[Na+].Cl>O>[I:11][C:9]1[CH:8]=[CH:7][C:3]([C:4]([OH:6])=[O:5])=[C:2]([NH:1][S:22]([C:17]2[C:16]3[N:15]=[CH:14][CH:13]=[N:12][C:21]=3[CH:20]=[CH:19][CH:18]=2)(=[O:23])=[O:24])[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium Carbonate2×HCID 16090697Quinoxaline-5-sulfonyl chlorideHCID 227247802-Amino-4-iodo-benzoic acid

Product 1

HCID 160907584-Iodo-2-(quinoxaline-5-sulfonylamino)benzoic acidYield 98.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-amino-4-iodo-benzoic acid (10 g, 38 mmol, 1.0 equiv.) and quinoxaline-5-sulfonyl chloride (8.7 g, 38 mmol) in 100 mL of water was basified with satd. aq. Na2CO3, with stirring, to adjust the pH to 8.0. As the reaction progressed, the pH was maintained at 8.0±0.2 by adding satd. aq. Na2CO3. After 3 h, no further pH changes were observed. The reaction mixture was stirred at rt for another 16 h. Conc. HCl was added to adjust the pH to <2. The precipitated solid was collected by filtration, washed with water and dried to afford the title compound as white solid (17 g, 37.4 mmol, 98%). MS (ESI+): calcd. for C15H10IN3O4S, 455.0; m/z found, 456 [M+H]+. 1H NMR (500 MHz, DMSO-d6): 14.0 (br s, 1H), 11.6 (s, 1H), 9.10 (d, J=1.5, 1H), 9.97 (d, J=1.5, 1H), 8.60 (d, J=7.4, 1H), 8.42 (d, J=8.4, 1H), 8.06 (t, J=7.5, 1H), 7.95 (d, J=1.2, 1H), 7.51 (d, J=8.3, 1H), 7.37 (dd, J=8.3, 1.2, 1H).

Workup

  1. temperaturethe pH was maintained at 8.0±0.2
  2. additionby adding satd
  3. filtrationThe precipitated solid was collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-d42b182f5f2e405c973c0f96a5d0a825
Source dataset
uspto-grants-2010_12
Patent number
US07855292B2

Reaction notes

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