Hydrochloric Acid → N-(3-nitrophenyl)methanesulfonamide

HRID 2398713Notes

Reaction equation

HRID 2398713 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][CH:10]=1)[NH2:7])([O-:3])=[O:2].[CH3:11][S:12](Cl)(=[O:14])=[O:13].Cl>N1C=CC=CC=1>[CH3:11][S:12]([NH:7][C:6]1[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:10]=[CH:9][CH:8]=1)(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 74233-NitroanilineHCID 31297Methanesulfonyl chloride

Product 1

HCID 843283N-(3-nitrophenyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 2.76 g. (0.02 mol) of m-nitroaniline in 5 ml. of pyridine cooled to 0° C. is added 1.6 ml. (0.02 mol) of methanesulfonyl chloride dropwise and the mixture is stirred at room temperature for two hours. The reaction mixture is decomposed by addition of dilute hydrochloric acid and ice, and dried to give m-(methylsulfonamido)-nitrobenzene, m.p. 237° C. The latter, 1.08 g. (0.005 mol), is dissolved in 100 ml. of ethanol, 300 mg. of 10% palladium-on-carbon is added and the mixture is hydrogenated in a Parr shaker. After hydrogen uptake has ceased, the catalyst is filtered off leaving the product, 3-methylsulfonamidoaniline, in solution. To this solution (100 ml. ethanol) is added 1.08 g. (0.005 mol) of 3,5-diacetyl-4,6-dihydroxy-2H-pyran-2-one and the solution is refluxed for one hour. The reaction mixture is concentrated and filtered to yield 5-acetyl-4-hydroxy-3-[1-(3-methylsulfonamidophenylamino)ethylidene]-2H-pyran-2,6(3H)-dione, m.p. 196° C.

Workup

  1. additionis added 1.6 ml
  2. customdried

Sources & evidence

ORD record
ord-8aac7666ee9d49968f6a2db38d328d8f
Source dataset
uspto-grants-1977_05
Patent number
US04025614

Reaction notes

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