Chlorobenzene → HCID 10317688, compound

HRID 447224

Reaction equation

HRID 447224 reaction equation
[CH3:1][N:2]([CH3:21])/[CH:3]=[N:4]/[S:5]([C:8]1[C:9]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1)(=[O:7])=[O:6].C1C(=O)N([Br:29])C(=O)C1.ClC1C=CC=CC=1>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>[CH3:1][N:2]([CH3:21])/[CH:3]=[N:4]/[S:5]([C:8]1[C:9]([C:14]2[CH:15]=[CH:16][C:17]([CH2:20][Br:29])=[CH:18][CH:19]=2)=[CH:10][CH:11]=[CH:12][CH:13]=1)(=[O:6])=[O:7]

Participants

6

Reactant 3

HCID 7964ChlorobenzeneHCID 67184N-bromobutanimideHCID 9972170N,N-dimethyl-N'-[2-(4-methylphenyl)phenyl]sulfonylmethanimidamide

Product 1

HCID 10317688HCID 10317688, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

4′-Methylbiphenyl-2-sulfonic acid 1-dimethylaminometh-(E)-ylideneamide (540.0 mg, 1786 μmol), NBS (318 mg, 1.8 mmol), and benzoyl peroxide (4.3 mg, 17.8 μmol) were dissolved in chlorobenzene (7.0 mL, 69 mmol) and the resulting solution was heated at 100° C. for 90 minutes. The mixture was cooled to room temperature and water was added. The mixture was extracted with DCM, washed with saturated NaHCO3 and saturated aqueous NaCl, extracted again with DCM, dried over MgSO4, filtered, and concentrated. The crude product was purified by flash chromatography (40 g, 0-100% EtOAc in hexanes), then taken up in EtOAc (4.5 mL) and DCM (1.5 mL). Additional DCM (3.0 mL) was added and the mixture was heated at 60° C. The mixture was cooled in the freezer overnight, then concentrated. The material was taken up in DCM (2 mL), EtOAc (6 mL) was added, and the resulting solution placed in the freezer. A precipitate formed and was filtered to yield the title compound (279 mg) as a white solid.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionThe mixture was extracted with DCM
  3. washwashed with saturated NaHCO3 and saturated aqueous NaCl
  4. extractionextracted again with DCM
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by flash chromatography (40 g, 0-100% EtOAc in hexanes)
  9. additionAdditional DCM (3.0 mL) was added
  10. temperaturethe mixture was heated at 60° C
  11. temperatureThe mixture was cooled in the freezer overnight
  12. concentrationconcentrated
  13. additionEtOAc (6 mL) was added
  14. customA precipitate formed
  15. filtrationwas filtered

Sources & evidence

ORD record
ord-a0954227e54f42939031ea246f17d11f
Source dataset
uspto-grants-2013_07
Patent number
US08481549B2

Linked notes

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