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Methylamine → 4-(3-(N-methylcarbamoyl)-4-methoxyphenoxy)-1-nitrobenzene

HRID 2078550
Notes
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Reaction equation

HRID 2078550 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)(O)=[O:2].O=S(Cl)Cl.[CH3:26][NH2:27].[OH-].[Na+]>C(Cl)Cl>[CH3:26][NH:27][C:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[O:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6329MethylamineHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 230230632-Methoxy-5-(4-nitrophenoxy)benzoic acid

Product 1

HCID 206091394-(3-(N-methylcarbamoyl)-4-methoxyphenoxy)-1-nitrobenzeneYield 95%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

To a solution of 4-(3-carboxy-4-methoxyphenoxy)-1-nitrobenzene (0.50 g, 1.75 mmol) in CH2Cl2 (12 mL) was added SOCl2 (0.64 mL, 8.77 mmol) in portions. The resulting solution was heated at the reflux temp. for 18 h, cooled to room temp., and concentrated under reduced pressure. The resulting yellow solids were dissolved in CH2Cl2 (3 mL) then the resulting solution was treated with a methylamine solution (2.0 M in THF, 3.5 mL, 7.02 mmol) in portions (CAUTION: gas evolution), and stirred at room temp. for 4 h. The resulting mixture was treated with a 1N NaOH solution, then extracted with CH2Cl2 (25 mL). The organic layer was dried (Na2SO4) and concentrated under reduced pressure to give 4-(3-(N-methylcarbamoyl)-4-methoxyphenoxy)-1-nitrobenzene as a yellow solid (0.50 g, 95%).

Workup

  1. temperatureThe resulting solution was heated at the reflux temp
  2. temperaturecooled to room temp.
  3. concentrationconcentrated under reduced pressure
  4. dissolutionThe resulting yellow solids were dissolved in CH2Cl2 (3 mL)
  5. extractionextracted with CH2Cl2 (25 mL)
  6. dry with materialThe organic layer was dried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b054ea9e2516439ab5ce5d331f7c9446
Source dataset
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07928239B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes