M-Phenylenediamine → HCID 43602671, compound

HRID 541819Notes

Reaction equation

HRID 541819 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[C:3]([NH2:7])[CH:2]=1.O1CCCC1.C(N(CC)CC)C.[N+:21]([C:24]1[CH:25]=[C:26]([S:30](Cl)(=[O:32])=[O:31])[CH:27]=[CH:28][CH:29]=1)([O-:23])=[O:22]>O.CCOC(C)=O>[NH2:7][C:3]1[CH:2]=[C:1]([NH:8][S:30]([C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=2)(=[O:31])=[O:32])[CH:6]=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 7935M-PhenylenediamineHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 84763-Nitrobenzenesulfonyl chloride

Product 1

HCID 43602671HCID 43602671, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Into a 1-neck round-bottom flask were added m-phenylenediamine (1.6 g, 14 mmol) and tetrahydrofuran (30 mL) and triethylamine (2.0 mL, 14 mmol). The mixture was cooled in ice bath and then m-nitrobenzenesulfonyl chloride (2.1 g, 9.6 mmol) was slowly added. The resultant mixture was warmed up to rt. after 1 h and EtOAc and water were then added. Aqueous layer was extracted again with EtOAc. The organics layers were combined, dried over Na2SO4 and the solvent was removed under vacuum. The crude was purified by silica gel column chromatography to give the desired product (2.5 g, 89%). LCMS for C12H11N3O4S (M+H)+: m/z=294.0. 1H NMR (300 MHz, CD3OD): δ 8.56 (t, J=2.0 Hz, 1H), 8.40 (ddd, J=8.2, 2.3, 1.2 Hz, 1H), 8.09 (ddd, J=7.8, 1.7, 1.0 HZ, 1H), 7.73 (t, J=8.1 Hz, 1H), 6.91 (t, J=8.1 Hz, 1H), 6.51 (t, J=2.2 Hz, 1H), 6.42 (ddd, J=8.1, 2.2, 1.0 Hz, 1H), 6.36 (ddd, J=7.9, 2.1, 1.0 Hz, 1H).

Workup

  1. temperatureThe mixture was cooled in ice bath
  2. extractionAqueous layer was extracted again with EtOAc
  3. dry with materialdried over Na2SO4
  4. customthe solvent was removed under vacuum
  5. customThe crude was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f69ab308dea44f5d95f1bacd4ec6359b
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Reaction notes

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