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Dimethylamine → 3-(4-Chloro-2-nitro-phenoxy)-N,N-dimethyl-benzamide

HRID 2358742
Notes
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Reaction equation

HRID 2358742 reaction equation
[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10](Cl)=[O:11])=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1.[CH3:21][NH:22][CH3:23].O>C1COCC1>[Cl:1][C:2]1[CH:17]=[CH:16][C:5]([O:6][C:7]2[CH:8]=[C:9]([CH:13]=[CH:14][CH:15]=2)[C:10]([N:22]([CH3:23])[CH3:21])=[O:11])=[C:4]([N+:18]([O-:20])=[O:19])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 674DimethylamineHCID 962WaterHCID 866155003-(4-Chloro-2-nitro-phenoxy)-benzoyl chloride

Product 1

HCID 684583013-(4-Chloro-2-nitro-phenoxy)-N,N-dimethyl-benzamideYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the product from Example 168b (2.0 g, 6.4 mmol) in THF (25 mL) was added dimethylamine (0.6 g, 13.3 mmol) and the reaction stirred for 16 h. The reaction was poured into water and extracted with ethyl acetate. The organic layer washed with 5% HCL, water, brine, and dried over sodium sulfate, filtered and concentrated under vacuum giving the title compound (1.9 g, 87%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer washed with 5% HCL, water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0b8e9d580d34458bb7191f4572b81d84
Source dataset
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07763731B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes