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N-[2-(4-nitroanilino)ethyl]methanesulfonamide → N-methyl-N-[2-(4-nitrophenylamino)ethyl]methanesulfonamide

HRID 1393836
Notes
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Reaction equation

HRID 1393836 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH2:11][CH2:12][NH:13][S:14]([CH3:17])(=[O:16])=[O:15])=[CH:6][CH:5]=1)([O-:3])=[O:2].S([O-])(O[CH3:22])(=O)=O>[OH-].[Na+]>[CH3:22][N:13]([CH2:12][CH2:11][NH:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[S:14]([CH3:17])(=[O:16])=[O:15]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 2847338N-[2-(4-nitroanilino)ethyl]methanesulfonamideHCID 4694097Methyl sulfate(1-)

Product 1

HCID 23104462N-methyl-N-[2-(4-nitrophenylamino)ethyl]methanesulfonamideYield 48.7%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
30 °C

Procedure

25.9 g (0.1 mol) of N-[2-(4-nitrophenylamino)ethyl]methanesulfonamide (22) were dissolved in 200 mL of 1N sodium hydroxide at 50° C. The insoluble matter was filtered off, the filtrate was cooled to 30° C. and 11.4 mL (0.12 mol) of methyl sulfate were added dropwise. The mixture was stirred for 1 hour at room temperature and then heated to 40° C. and the yellow precipitate was filtered off. The product was reslurried in 0.5N sodium hydroxide and in water. The wet crude product was recrystallized from 50 mL of 96% ethanol with carbon black. 13.3 g of product with a melting point of 109° C. were isolated.

Workup

  1. filtrationThe insoluble matter was filtered off
  2. temperatureheated to 40° C.
  3. filtrationthe yellow precipitate was filtered off
  4. customThe wet crude product was recrystallized from 50 mL of 96% ethanol with carbon black

Sources & evidence

ORD record
ord-bc3cf21ee81648e88a9a555567bdddee
Source dataset
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07347879B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes