Benzylamine → Benzenemethanesulfonamide

HRID 874183Notes

Reaction equation

HRID 874183 reaction equation
[CH2:1](N)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([N:11](CC)CC)C.C[S:17](Cl)(=[O:19])=[O:18]>ClCCl>[CH2:1]([S:17]([NH2:11])(=[O:19])=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride

Product 1

HCID 78318BenzenemethanesulfonamideYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Previous intermediate from step 1 was dissolved in 2 mL of dichloromethane and triethylamine (0.035 mL, 0.249 mmol) was added. Solution was cooled to 0° C. and methane sulfonylchloride (0.020 mL, 0.238 mmol) was added. Reaction mixture was warmed to room temperature, stirred overnight, then concentrated under reduced pressure. Residue was purified by silica gel column chromatography (10-90% ethyl acetate in hexanes) to yield the intermediate benzylsulfonamide (35 mg, 78%).

Workup

  1. customReaction mixture
  2. temperaturewas warmed to room temperature
  3. concentrationconcentrated under reduced pressure
  4. customResidue was purified by silica gel column chromatography (10-90% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-8b5d5fae4ac54d92affd8ac304b5aea8
Source dataset
uspto-grants-2015_03
Patent number
US08980878B2

Reaction notes

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