O-Phenylenediamine → Benzo[b]thiophene-2-sulfonic acid (2-aminophenyl)amide

HRID 730204Notes

Reaction equation

HRID 730204 reaction equation
[C:1]1([NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH2:7].[S:9]1[C:13]([S:14](Cl)(=[O:16])=[O:15])=[CH:12][C:11]2[CH:18]=[CH:19][CH:20]=[CH:21][C:10]1=2>C(Cl)Cl.N1C=CC=CC=1>[NH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=1[NH:8][S:14]([C:13]1[S:9][C:10]2[CH:21]=[CH:20][CH:19]=[CH:18][C:11]=2[CH:12]=1)(=[O:15])=[O:16]

Participants

5

Reactant 2

HCID 7243O-PhenylenediamineHCID 27763331-Benzothiophene-2-sulfonyl chloride

Product 1

HCID 86240018Benzo[b]thiophene-2-sulfonic acid (2-aminophenyl)amideYield 78.8%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of o-phenylenediamine (5 mmol) in DCM (25 mL) and pyridine (5 mL) at 0° C., benzo[b]thiophene-2-sulfonyl chloride (5.5 mmol) was added in small portions. The reaction mixture was then gradually warmed to RT with stirring continued until the reaction was complete as determined by TLC or LC-MS. The reaction mixture was then diluted with DCM (25 mL). The organic phase was washed with water (2×25 mL) and 25 mL of brine. 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/EtOAc to give 1.2 g of benzo[b]thiophene-2-sulfonic acid (2-amino-phenyl)-amide. Tr 0.94 min, MS: 305.7 (M+1)+. 1H NMR (DMSO-d6, 400 MHz): δ 6.40 (t, 1H), 6.60 (d, 1H), 6.78 (d, 1H), 6.89 (t, 1H), 7.45 (t, 1H), 7.50 (t, 1H), 7.80 (s, 1H), 7.90 (d, 1H), 8.80 (d, 1H) ppm.

Workup

  1. washThe organic phase was washed with water (2×25 mL) and 25 mL of brine
  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/EtOAc

Sources & evidence

ORD record
ord-0333576690ca4bb69fc2dd94fdf11d9f
Source dataset
uspto-grants-2009_09
Patent number
US07582673B2

Reaction notes

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