Methanesulfonyl chloride → N-(3-ethynylphenyl)methanesulfonamide

HRID 238156Notes

Reaction equation

HRID 238156 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:7]=[CH:8][CH:9]=1)[NH2:6])#[CH:2].[CH3:10][S:11](Cl)(=[O:13])=[O:12]>N1C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([NH:6][S:11]([CH3:10])(=[O:13])=[O:12])[CH:7]=[CH:8][CH:9]=1)#[CH:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 104682Benzenamine, 3-ethynyl-

Product 1

HCID 57131399N-(3-ethynylphenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-ethynyl aniline (1.05 mL, 10.0 mmol) in pyridine (5 mL) was added methanesulfonyl chloride (857 μL, 1.10 eq.) at a temperature of 0° C. The resulting mixture was stirred overnight at room temperature and was then evaporated. The residue was treated with 2 N aq. HCl (25 mL) and subsequently extracted with ethyl acetate (2×30 mL). The combined organic layers were dried over MgSO4 and evaporated to give the desired methanesulfonamide in quantitative yield. It was used without further purification.

Workup

  1. customwas then evaporated
  2. additionThe residue was treated with 2 N aq. HCl (25 mL)
  3. extractionsubsequently extracted with ethyl acetate (2×30 mL)
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. customevaporated

Sources & evidence

ORD record
ord-e274d04f6bca41a48a5d7aaab5b94c20
Source dataset
uspto-grants-2014_02
Patent number
US08642611B2

Reaction notes

Loading…