O-Phenylenediamine → HCID 11648442, compound

HRID 730231Notes

Reaction equation

HRID 730231 reaction equation
[C:1]1([NH2:8])[C:2]([NH2:7])=[CH:3][CH:4]=[CH:5][CH:6]=1.[O:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:11]=[C:10]1[S:18](Cl)(=[O:20])=[O:19]>C(Cl)Cl.N1C=CC=CC=1>[O:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:11]=[C:10]1[S:18]([NH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH:8][S:18]([C:10]1[O:9][C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[CH:11]=1)(=[O:19])=[O:20])(=[O:20])=[O:19]

Participants

5

Reactant 2

HCID 7243O-PhenylenediamineHCID 27951721-Benzofuran-2-sulfonyl chloride

Product 1

HCID 11648442HCID 11648442, compoundYield 49.9%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of benzene-1,2-diamine (0.5 mmol) in DCM (2 mL) and pyridine (0.5 mL) at 0° C., benzofuran-2-sulfonyl chloride (1.1 mmol; prepared as in Example 12) was added at 0° C. in small portions over 10-15 min. The reaction mixture was then gradually warmed to RT with stirring continued for 6 h. The reaction mixture was then diluted with DCM (5 mL). The organic phase was washed with 10% aqueous HCl (5 mL), water (5 mL), and brine (5 mL). The organic phase was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue obtained was purified by flash column chromatography eluting with DCM followed by EtOAc/DCM (1% to 3%) to give 117 mg of N-{2-[(1-benzofuran-2-ylsulfonyl)amino]phenyl}-1-benzofuran-2-sulfonamide. Tr 1.18 min; MS: 469.7 (M+1)+.

Workup

  1. washThe organic phase was washed with 10% aqueous HCl (5 mL), water (5 mL), and brine (5 mL)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe residue obtained
  5. customwas purified by flash column chromatography
  6. washeluting with DCM

Sources & evidence

ORD record
ord-49d1f7f01a464d9ead6398b0b99f0d8b
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

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