2,4,6-Tris(1-methylethyl)benzenesulfonyl chloride → HCID 75203092, compound

HRID 1749127Notes

Reaction equation

HRID 1749127 reaction equation
[CH:1]([C:4]1[CH:9]=[C:8]([CH:10]([CH3:12])[CH3:11])[CH:7]=[C:6]([CH:13]([CH3:15])[CH3:14])[C:5]=1[S:16](Cl)(=[O:18])=[O:17])([CH3:3])[CH3:2].[Br:20][C:21]1[C:27]([C:28]([F:31])([F:30])[F:29])=[CH:26][C:25]([C:32]([F:35])([F:34])[F:33])=[CH:24][C:22]=1[NH2:23]>N1C=CC=CC=1>[Br:20][C:21]1[C:27]([C:28]([F:30])([F:31])[F:29])=[CH:26][C:25]([C:32]([F:33])([F:34])[F:35])=[CH:24][C:22]=1[NH:23][S:16]([C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][C:8]([CH:10]([CH3:12])[CH3:11])=[CH:7][C:6]=1[CH:13]([CH3:15])[CH3:14])(=[O:18])=[O:17]

Participants

4

Reactant 2

HCID 810422,4,6-Tris(1-methylethyl)benzenesulfonyl chlorideHCID 43054482-Bromo-3,5-bis(trifluoromethyl)aniline

Product 1

HCID 75203092HCID 75203092, compoundYield 4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2,4,6-Triisopropyl-benzenesulfonyl chloride (0.491 g, 1.59 mmol) was added to a solution of 2-bromo-3,5-bis(trifluoromethyl)aniline (0.483 g, 1.59 mmol) in dry pyridine (1 mL). The reaction was capped and stirred at room temperature for 1 day then stirred at 30° C. for 1 day. The reaction was then concentrated under vacuum. To this was added diethyl ether (100 mL) and the mixture was washed with 0.1 N HCl (3×30 mL) followed by 0.1 N NaOH (2×30 mL) then saturated NaCl (2×30 mL). After drying the organic layer over MgSO4, the solution was filtered and concentrated under vacuum. The crude compound was purified by silica gel chromatography using hexanes/ethyl acetate (10:1) to afford the title compound (0.036 g, 4% yield). LCMS (M+Na) 597.

Workup

  1. customThe reaction was capped
  2. stirringthen stirred at 30° C. for 1 day
  3. concentrationThe reaction was then concentrated under vacuum
  4. additionTo this was added diethyl ether (100 mL)
  5. washthe mixture was washed with 0.1 N HCl (3×30 mL)
  6. dry with materialAfter drying the organic layer over MgSO4
  7. filtrationthe solution was filtered
  8. concentrationconcentrated under vacuum
  9. customThe crude compound was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5d7470fde15e4f1aadc06a64ca809f91
Source dataset
uspto-grants-2015_10
Patent number
US09156781B2

Reaction notes

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