Dimethylamine → 4-(Bromomethyl)-N,N-dimethylbenzenesulfonamide

HRID 1867132Notes

Reaction equation

HRID 1867132 reaction equation
[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9](Cl)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[CH3:13][NH:14][CH3:15].C(N(CC)C(C)C)(C)C>O1CCCC1>[Br:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:14]([CH3:15])[CH3:13])(=[O:11])=[O:10])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 81531DiisopropylethylamineHCID 27344094-(Bromomethyl)benzenesulfonyl chloride

Product 1

HCID 110440824-(Bromomethyl)-N,N-dimethylbenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(Bromomethyl)benzenesulfonyl chloride (5.0 g, 18.6 mmol) was dissolved in tetrahydrofuran. N,N-dimethylamine (7.7 mL, 15.5 mmol, 2M in tetrahydrofuran) and N,N-diisopropylethylamine (3.5 mL, 20.1 mmol) were added, and the reaction was allowed to stir at ambient temperature for 2 hours. The reaction was concentrated to an oil that was partitioned between water and ethyl acetate and extracted with ethyl acetate. The organic extracts were combined, washed with brine, dried over Na2SO4, and filtered. The resulting filtrate was concentrated to an oil which deposited needles that were a mixture of the title compound and 4-chloromethyl N,N-dimethylbenzenesulfonamide The resulting needles were collected and dried (2.3 g, 44%). ES-MS m/z 534 (M+H) and 578 (M+H).

Workup

  1. concentrationThe reaction was concentrated to an oil that
  2. customwas partitioned between water and ethyl acetate
  3. extractionextracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationThe resulting filtrate was concentrated to an oil which
  8. additiona mixture of the title compound and 4-chloromethyl N,N-dimethylbenzenesulfonamide The resulting needles
  9. customwere collected
  10. customdried (2.3 g, 44%)

Sources & evidence

ORD record
ord-e9e0fb4db8a545ffa66f6b982383eff2
Source dataset
uspto-grants-2009_12
Patent number
US07629363B2

Reaction notes

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