Hydrochloric Acid → N-(3,5-Dichlorophenyl)-N-methyl-3-nitrobenzamide

HRID 2086817Notes

Reaction equation

HRID 2086817 reaction equation
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]([CH:20]=[CH:21][CH:22]=1)[C:9]([NH:11][C:12]1[CH:17]=[C:16]([Cl:18])[CH:15]=[C:14]([Cl:19])[CH:13]=1)=[O:10])([O-:5])=[O:4].I[CH3:24].Cl>CN(C)C=O>[N+:3]([C:6]1[CH:7]=[C:8]([CH:20]=[CH:21][CH:22]=1)[C:9]([N:11]([CH3:24])[C:12]1[CH:13]=[C:14]([Cl:19])[CH:15]=[C:16]([Cl:18])[CH:17]=1)=[O:10])([O-:5])=[O:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 711488HCID 711488, compound

Product 1

HCID 22724343N-(3,5-Dichlorophenyl)-N-methyl-3-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (60% in oil, 1.1 g) in N,N-dimethylformamide (20 ml) was added dropwise a solution of 3-nitro-N-(3,5-dichlorophenyl)benzamide (5.89 g) in N,N-dimethylformamide (40 ml). The mixture was stirred at room temperature for 1 hour, then iodomethane (3 ml) was added thereto. After stirring at room temperature for 1 hour, dilute hydrochloric acid was added to the mixture and extracted with ethyl acetate twice. The combined organic solution was washed with water and brine, dried over magnesium sulfate and concentrated. The residue was solidified with isopropyl ether to give 3-nitro-N-methyl-N-(3,5-dichlorophenyl)benzamide (4.62 g).

Workup

  1. stirringAfter stirring at room temperature for 1 hour
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic solution was washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-2f88931b80ab45fd98cea6bda424e45c
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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