Methanesulfonyl chloride → HCID 425315, compound

HRID 1090354Notes

Reaction equation

HRID 1090354 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH3:6][N:7]([CH3:11])[CH2:8][CH2:9][NH2:10].C(N(C(C)C)CC)(C)C>O1CCCC1>[CH3:6][N:7]([CH3:11])[CH2:8][CH2:9][NH:10][S:2]([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chloride2×HCID 66053N,N-DimethylethylenediamineHCID 81531Diisopropylethylamine

Product 1

HCID 425315HCID 425315, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (Compound 19, 2.6 ml, 34.0 mmol) was added to a mixture of N,N-dimethylethylenediamine (3.7 ml, 34.0 mmol) and diisopropylethylamine (5.93 ml, 34.0 mmol) in tetrahydrofuran (30 ml) at 0° C. After 1.5 hours stirring at 0°, the mixture was quenched with water and extracted thoroughly with ethyl acetate. Evaporation of the dried (magnesium sulfate) extract gave an oil, which was purified by flash chromatography on silica using 20% methanol/chloroform to give the title sulfonamide. 1HNMR(CDCl3): 2.24 (s, 6H), 2.48 (t, 2H, J=5.9 Hz), 2.97 (s, 3H), 3.18 (t, 2H, J=5.6 Hz). 13CNMR(CDCl3): 39.3, 39.9, 44.5 and 57.8.

Workup

  1. customthe mixture was quenched with water
  2. extractionextracted thoroughly with ethyl acetate
  3. customEvaporation of the
  4. dry with materialdried (magnesium sulfate)
  5. extractionextract
  6. customgave an oil, which
  7. customwas purified by flash chromatography on silica using 20% methanol/chloroform

Sources & evidence

ORD record
ord-a2fd01eb419a4a4384cf795715139d21
Source dataset
uspto-grants-1992_01
Patent number
US05081261

Reaction notes

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