P-Toluenesulfonamide → 5-Bromo-2-(p-tolylsulfonyl)isoindoline

HRID 2208584Notes

Reaction equation

HRID 2208584 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:5]=[CH:6][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:8][CH:9]=1.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Br)=[C:17]([CH2:23]Br)[CH:16]=1>CN(C)C(=O)C.CCOCC>[Br:14][C:15]1[CH:16]=[C:17]2[C:18](=[CH:19][CH:20]=1)[CH2:21][N:13]([S:10]([C:7]1[CH:6]=[CH:5][C:4]([CH3:3])=[CH:9][CH:8]=1)(=[O:12])=[O:11])[CH2:23]2

Participants

6

Reactant 3

HCID 6269P-ToluenesulfonamideHCID 24758Sodium hydrideHCID 124964654-Bromo-1,2-bis(bromomethyl)benzene

Product 1

HCID 151678985-Bromo-2-(p-tolylsulfonyl)isoindoline

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 31374DimethylacetamideSolvent3×

Procedure

To a suspension of sodium hydride (440 mg, 60% dispersion in mineral oil, 11 mmol) in N,N-dimethylacetamide (24 mL) was added, dropwise, a solution of p-toluenesulfonamide (1.45 g, 8.5 mmol) in N,N-dimethylacetamide (8 mL) over about 5 min. The frothy solution was stirred for 1 hr at room temperature then heated to 60° C. and stirred at this temperature for 0.5 hr. To this mixture was added, dropwise a solution of 4-bromo-1,2-bis(bromomethyl)benzene (2.9 g 8.4 mmol) in N,N-dimethylacetamide (6 mL). The resulting mixture was stirred for 1 hr then cooled to room temperature and stirred for 17 hr. The mixture was then diluted with ether, washed with water (2×) then brine, dried over sodium sulfate and concentrated. The residue was triturated with ethyl acetate and filtered to give the title compound as a white solid.

Workup

  1. additionwas added
  2. temperaturethen heated to 60° C.
  3. stirringstirred at this temperature for 0.5 hr
  4. additionTo this mixture was added
  5. stirringThe resulting mixture was stirred for 1 hr
  6. temperaturethen cooled to room temperature
  7. stirringstirred for 17 hr
  8. washwashed with water (2×)
  9. dry with materialbrine, dried over sodium sulfate
  10. concentrationconcentrated
  11. customThe residue was triturated with ethyl acetate
  12. filtrationfiltered

Sources & evidence

ORD record
ord-04458fc51b2b440b8b0b6920da3ae6d6
Source dataset
uspto-grants-2016_06
Patent number
US09376454B2

Reaction notes

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