Ammonia → 4,4-Dimethylpentane-1-sulfonamide

HRID 397274Notes

Reaction equation

HRID 397274 reaction equation
[NH3:1].[CH3:2][C:3]([CH3:12])([CH3:11])[CH2:4][CH2:5][CH2:6][S:7](Cl)(=[O:9])=[O:8]>O1CCCC1>[CH3:2][C:3]([CH3:12])([CH3:11])[CH2:4][CH2:5][CH2:6][S:7]([NH2:1])(=[O:9])=[O:8]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 835316364,4-Dimethylpentane-1-sulfonyl chloride

Product 1

HCID 865842554,4-Dimethylpentane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Anhydrous ammonia gas was passed into a solution of 4,4-dimethylpentane sulphonyl chloride (1.85 g) in dry tetrahydrofuran (5 ml) at 5-10° C. until saturation. The resulting suspension was stirred at room temperature for 18 hours and then evaporated under reduced pressure. The residue was partitioned between ethyl acetate (20 ml) and 2N aqueous hydrochloric acid (20 ml). The organic phase was separated, washed (brine 20 ml), dried (Na2SO4) and evaporated. Column chromatography on silica eluting with dichloromethane:methanol 98:2 gave 4,4-dimethylpentane sulphonic acid amide as an off-white solid (0.72 g).

Workup

  1. customevaporated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate (20 ml) and 2N aqueous hydrochloric acid (20 ml)
  3. customThe organic phase was separated
  4. washwashed (brine 20 ml)
  5. dry with materialdried (Na2SO4)
  6. customevaporated

Sources & evidence

ORD record
ord-53f60ff02f1a4e9892e5b6138e9d2412
Source dataset
uspto-grants-2003_08
Patent number
US06610518B2

Reaction notes

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