Methanesulfonyl chloride → N-(4-Acetyl-2-methylphenyl)methanesulfonamide

HRID 466351

Reaction equation

HRID 466351 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH3:11].[CH3:12][S:13](Cl)(=[O:15])=[O:14]>N1C=CC=CC=1.O1CCCC1>[CH3:11][C:3]1[CH:4]=[C:5]([C:8](=[O:10])[CH3:9])[CH:6]=[CH:7][C:2]=1[NH:1][S:13]([CH3:12])(=[O:15])=[O:14]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 133555151-(4-Amino-3-methylphenyl)ethan-1-one

Product 1

HCID 19873430N-(4-Acetyl-2-methylphenyl)methanesulfonamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

4'-Amino-3'-methylacetophenone from Step VIII (3.0 g, 20 mmol) in 15 ml of dry pyridine at 5° C. is reacted with 3.0 g (26.2 mmol) of methanesulfonyl chloride in 5 ml of tetrahydrofuran. The reaction is stirred at 5° C. for 2 hrs, then at room temperature overnight. The reaction is diluted with ice-water. The solid is collected, washed with water, air dried and crystallized from methylene chloride-pet. ether to yield the title compound; m.p. 152°-153° C.

Workup

  1. customat room temperature
  2. customovernight
  3. customThe solid is collected
  4. washwashed with water, air
  5. customdried
  6. customcrystallized from methylene chloride-pet. ether

Sources & evidence

ORD record
ord-0ac4085aa85945ca8f78d814c4565448
Source dataset
uspto-grants-1992_10
Patent number
US05155268

Linked notes

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