Dimethyl Sulfate → HCID 601943, compound

HRID 59278Notes

Reaction equation

HRID 59278 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][C:5]([NH2:6])=[C:4]([N+:10]([O-:12])=[O:11])[CH:3]=1.[OH-].[Na+].S(OC)(O[CH3:19])(=O)=O>C1(C)C=CC=CC=1>[CH3:19][NH:6][C:5]1[CH:7]=[C:8]([CH3:9])[C:2]([CH3:1])=[CH:3][C:4]=1[N+:10]([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14798Sodium HydroxideHCID 814454,5-Dimethyl-2-nitrobenzenamine

Product 1

HCID 601943HCID 601943, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 4,5-dimethyl-2-nitroaniline (2.00 g, 12 mmol) in toluene (25 mL) was added NaOH (1.93 g, 48 mmol). The reaction mass was stirred at 100° C. for 1 h, followed by addition of dimethyl sulphate (4.6 g, 36 mmol) and reaction mass was stirred at RT for 24 h. The reaction mass was quenched in water, extracted with DCM and concentrated to afford 1.5 g of desired product. 1H NMR (300 MHz, DMSO d6): δ 2.11 (s, 3H), 2.24 (d, J=7.8 Hz, 3H), 2.92 (s, 3H), 6.77 (m, 1H), 7.79 (m, 1H), 8.06 (s, 1H); MS (m/z): 180.92 (M+H)+.

Workup

  1. stirringwas stirred at RT for 24 h
  2. customThe reaction mass was quenched in water
  3. extractionextracted with DCM
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5b1757f46b4746dca18661e058db2ef1
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Reaction notes

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