Dimethyl Sulfate → 2,3-dichloro-N-methyl-6-nitroaniline

HRID 858158Notes

Reaction equation

HRID 858158 reaction equation
[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[NH2:4].[OH-].[Na+].[Cl-].[C:16]([NH3+])(C)(C)C.S(OC)(OC)(=O)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:8]([Cl:9])=[CH:7][CH:6]=[C:5]([N+:10]([O-:12])=[O:11])[C:3]=1[NH:4][CH3:16]

Participants

6

Reactant 4

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 30175542,3-Dichloro-6-nitroanilineHCID 11355454t-Butylammonium chloride

Product 1

HCID 204396362,3-dichloro-N-methyl-6-nitroaniline

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2,3-dichloro-6-nitroaniline (1.026 g, 5 mmole), was suspended in toluene (10 ml). To this vigorously stirred suspension was added 50% aqueous sodium hydroxide solution (1.7 g), tertiary-butyl ammonium chloride (0.07 g, 0.25 mmole) and dimethyl sulfate (0.51 ml, 5.4 mmole). After 4 hr stirring at room temperature the intense red solution was washed with water, brine, dried with magnesium sulfate, filtered, evaporated in vacuo. Weight=1.03 g, m.p.=82° C.

Workup

  1. washwas washed with water, brine
  2. dry with materialdried with magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-c8a6993f31c14c42bcc950de33867b1c
Source dataset
uspto-grants-2006_12
Patent number
US07148236B2

Reaction notes

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