Triethylamine → N-[4-(Cyanomethyl)phenyl]methanesulfonamide

HRID 1351408Notes

Reaction equation

HRID 1351408 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[NH2:6][C:7]1[CH:15]=[CH:14][C:10]([CH2:11][C:12]#[N:13])=[CH:9][CH:8]=1.C(N(CC)CC)C>ClCCl>[C:12]([CH2:11][C:10]1[CH:14]=[CH:15][C:7]([NH:6][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:8][CH:9]=1)#[N:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 770004-Aminophenylacetonitrile

Product 1

HCID 289747N-[4-(Cyanomethyl)phenyl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulphonyl chloride (3.22 ml, 41.6 mmol) was added dropwise to a solution of 4-aminobenzylcyanide (5.00 g, 37.8 mmol) and triethylamine (5.79 ml, 41.6 mmol) in dichloromethane (30 ml). The reaction mixture was stirred for 1 hour and then poured onto water, the organic layer was separated, dried (MgSO4), filtered and the solvent removed under reduced pressure to afford the title compound as a pale orange solid, 6.50 g.

Workup

  1. additionpoured onto water
  2. customthe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-b67cb0a34b5e41e89aa899704c710c16
Source dataset
uspto-grants-2007_05
Patent number
US07217714B1

Reaction notes

Loading…