Dimethylformamide → HCID 12046097, compound

HRID 2120094Notes

Reaction equation

HRID 2120094 reaction equation
[H-].[Na+].Br[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Br:10])[C:5]=1[S:11]([NH:14][C:15]([CH3:18])([CH3:17])[CH3:16])(=[O:13])=[O:12].[Li]CCCC.CN(C)[CH:26]=[O:27]>O1CCCC1>[Br:10][C:6]1[C:5]2[S:11](=[O:13])(=[O:12])[N:14]([C:15]([CH3:18])([CH3:17])[CH3:16])[CH:26]([OH:27])[C:4]=2[CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 12046096HCID 12046096, compoundHCID 178418339Butyllithium

Product 1

HCID 12046097HCID 12046097, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To sodium hydride (0.52 g, 12.9 mmol) in tetrahydrofuran (20 mL) at 0° C. was added 2,6-dibromo-N-(1,1-dimethylethyl) benzenesulfonamide (4.0 g, 10.8 mmol). The resulting mixture was stirred at ambient temperature for 2-3 h, cooled to −78° C. and treated with n-BuLi (1.6 M in hexanes, 7.4 mL, 11.9 mmol) over a period of 20 min. The reaction was continued to stir for 40 min and treated with N,N-dimethyl formamide (0.9 mL, 11.9 mL). The cooling bath was removed and the mixture continued to stir over a period of 20 min. The work-up consisted of slowly quenching the reaction with 1N NaCl, dilution with water and extraction with ethyl acetate. Drying over sodium sulfate and concentrating under reduced pressure provided the crude product that was purified by the flash chromatography (ethyl acetate/hexane, 1:4) to afford the 7-bromo-2-(1,1-dimethylethyl)-2,3-dihydro-1,2-benzisothiazol-3-ol 1,1-dioxide (2.1 g, 55%). 1H NMR (CD3OD): δ 1.61 (s, 9H), 6.02 (s, 1H), 7.61 (m, 2H), 7.77 (m, 1H).

Workup

  1. temperaturecooled to −78° C.
  2. stirringto stir for 40 min
  3. customThe cooling bath was removed
  4. stirringto stir over a period of 20 min
  5. customof slowly quenching
  6. customthe reaction with 1N NaCl, dilution
  7. extractionwith water and extraction with ethyl acetate
  8. dry with materialDrying over sodium sulfate
  9. concentrationconcentrating under reduced pressure
  10. customprovided the crude product that
  11. customwas purified by the flash chromatography (ethyl acetate/hexane, 1:4)

Sources & evidence

ORD record
ord-3774cb9aa7214218b2c0bed05b58c71b
Source dataset
uspto-grants-2004_02
Patent number
US06689770B2

Reaction notes

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