P-Anisidine → HCID 70691178, compound

HRID 1876451Notes

Reaction equation

HRID 1876451 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[CH3:15][O:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.C([O-])([O-])=O.[K+].[K+]>CS(C)=O>[Cl:8][C:6]1[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]([N+:12]([O-:14])=[O:13])=[C:2]([CH:7]=1)[NH:21][C:20]1[CH:22]=[CH:23][C:17]([O:16][CH3:15])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 11430Potassium CarbonateHCID 772861,3-Dichloro-4,6-dinitrobenzene

Product 1

HCID 70691178HCID 70691178, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

2,4-Dichloro-1,5-dinitrobenzene (II-1, 0.5 g, 2.11 mmol) and p-methoxyaniline (III-2, 0.2 g, 2.11 mmol) were dissolved in 5 mL DMSO. To the solution were added K2CO3 (0.58 g, 4.22 mmol) and metal Cu in catalytic amount. The mixture was allowed to react at 115° C. for 2 hours with stirring in an atmosphere of nitrogen. The resultant was poured into ice water, stirred to precipitate a solid. The solid was filtered, washed with water several times, dried, and separated on silica gel column (petroleum ether/ethyl acetate) to obtain a bronzing solid (IV-2, 0.68 g, 67%). 1H NMR (CDCl3) δ ppm 3.88 (3H, s, OCH3), 7.02 (1H, s, ArH-6), 7.03 (2H, d, J=8.96 Hz, ArH-3′, 5′), 7.21 (2H, d, J=8.96 Hz, ArH-2′, 6′), 9.07 (1H, s, ArH-3), 9.73 (1H, s, NH).

Workup

  1. customto react at 115° C. for 2 hours
  2. stirringstirred
  3. customto precipitate a solid
  4. filtrationThe solid was filtered
  5. washwashed with water several times
  6. customdried
  7. customseparated on silica gel column (petroleum ether/ethyl acetate)
  8. customto obtain a bronzing solid (IV-2, 0.68 g, 67%)

Sources & evidence

ORD record
ord-ad4c223951964800ad9844a3ae7c7d88
Source dataset
uspto-grants-2012_11
Patent number
US08309602B2

Reaction notes

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