Methanesulfonyl chloride → N-(2-chloro-4-cyano-6-methyl-phenyl)-methanesulfonamide

HRID 245092Notes

Reaction equation

HRID 245092 reaction equation
[NH2:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[Cl:11].[CH3:12][S:13](Cl)(=[O:15])=[O:14]>O>[Cl:11][C:3]1[CH:4]=[C:5]([C:6]#[N:7])[CH:8]=[C:9]([CH3:10])[C:2]=1[NH:1][S:13]([CH3:12])(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 27353014-Amino-3-chloro-5-methylbenzonitrile

Product 1

HCID 67491342N-(2-chloro-4-cyano-6-methyl-phenyl)-methanesulfonamideYield 46.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-amino-3-chloro-5-methylbenzonitrile (155 mg, 930 μmol) and methanesulfonylchloride (2.13 g, 18.6 mmol, 1.44 mL) is heated under microwave conditions to 150° C. for 7 h. The mixture is cooled to rt, diluted with water and extracted with EA. The org. extract is dried over MgSO4, filtered and concentrated. The crude product is purified on prep. TLC using heptane:EA 1:1 to give N-(2-chloro-4-cyano-6-methyl-phenyl)-methanesulfonamide (105 mg) as an orange solid; LC-MS**: tR=0.48 min; 1H NMR (CDCl3): δ2.59 (s, 3H), 3.18 (s, 3H), 6.27 (s, 1H), 7.55 (d, J=1.3 Hz, 1H), 7.65 (d, J=1.5 Hz, 1H).

Workup

  1. temperatureThe mixture is cooled to rt
  2. extractionextracted with EA
  3. extractionextract
  4. dry with materialis dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product is purified on prep

Sources & evidence

ORD record
ord-8530dfee55534750ac58336a156b10bb
Source dataset
uspto-grants-2014_02
Patent number
US08658675B2

Reaction notes

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