Methanesulfonyl chloride → N-(4-cyano-2-nitrophenyl)methanesulfonamide

HRID 2423352Notes

Reaction equation

HRID 2423352 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C1COCC1>[C:6]([C:5]1[CH:8]=[CH:9][C:2]([NH:1][S:14]([CH3:13])(=[O:16])=[O:15])=[C:3]([N+:10]([O-:12])=[O:11])[CH:4]=1)#[N:7]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 5959014-Amino-3-nitrobenzonitrile

Product 1

HCID 11630092N-(4-cyano-2-nitrophenyl)methanesulfonamideYield 16%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

KH (700 mg, 6.1 mmol) was dissolved in THF (15 mL) at −78° C. and to the solution was added dropwise the solution of 4-amino-3-nitro-benzonitrile (500 mg, 3.1 mmol) in THF (10 mL). After the reaction solution was stirred for 30 minutes, to the solution was added dropwisely methanesulfonyl chloride (0.35 mL, 4.6 mmol) and stirred for 3 hours. The reaction solution was quenched with water and the resulting solution was diluted with ethylacetate. The organic phase was washed with water and brine, dried over anhydride MgSO4 and concentrated under reduced pressure. The residue was purified with column chromatography (n-hexane/ethyl acetate=5/1) to yield the nitrile (120 mg, 16%).

Workup

  1. stirringstirred for 3 hours
  2. customThe reaction solution was quenched with water
  3. additionthe resulting solution was diluted with ethylacetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialdried over anhydride MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with column chromatography (n-hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-9f535c82791c4756aefd91055b079005
Source dataset
uspto-grants-2011_06
Patent number
US07960584B2

Reaction notes

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